2-Chloro-3-methylpyridine-4-carboxaldehyde

To a sol. of 2-chloro-3, N-dimethyl-N-phenylisonicotinamide (124.9 g, 479 mmol) inCHTo a sol. of 2-chloro-3, A/-dimethyl-iV-phenylisonicotinamide (124.9 g, 479 mmol) in CH2CI2 (1300 mL) was added at -78 °C DIBAL (1M in THF, 719 mL, 719 mmol) over 1 h, and the mixture was stirred for 2 h at this temperature. DIBAL (1M in THF, 281 mL, 281 mmol) was added again, and the reaction mixture was stirred at -60 °C for 30 min. Aq. sat. potassium sodium tartrate (500 mL) was added over 30 min, the cooling bath was removed, and the mixture was stirred overnight at rt. Water was added (100 mL), the org. phase was separated, and thewater phase was extracted with CHTo the sol. of pyridine derivative O (9.58 g, 36.7 mmol) in CH2CI2 (190 mL) was at-78 °C added DIBAL (1M in CH2C12, 55.1 mL, 55.1 mmol), and the mixture was stirred at-78 °C for 1.5 h. Aq. sat. tartaric acid monosodium monokalium salt in water (20 ml) was added and the mixture was allowed to warm up to rt. Water was added and the mixture was extracted with CH2Cl2. The org. extracts were dried over MgS04, filtered, and the solvents were removed under reduced pressure. Purification of the residue by FC yielded the title compound (4.4 g, 77percent). LC-MS: RT = 0.76 min; ES+ = 156.1.2-Chloro-3-methylpyridine-4-carbaldehyde (P); To the sol. of pyridine derivative O (9.58 g, 36.7 mmol) in CH2C12 (190 mL) was at-78 °C added DIBAL (1M in CH2C12, 55.1 mL, 55.1 mmol), and the mixture was stirred at-78 °C for 1.5 h. Aq. sat. tartaric acid monosodium monokalium salt in water (20 ml) was added and the mixture was allowed to warm up to rt. Water was added and the mixture was extracted with CH2C12. The org. extracts were dried over MgS04, filtered, and the solvents were removed under reduced pressure. Purification of the residue by FC yielded the title compound (4.4 g, 77percent). LC-MS: RT = 0.76 min; ES+ = 156. 1To the sol. of pyridine derivative O (9.58 g, 36.7 mmol) in CH2C12 (190 mL) was at-78 °C added DIBAL (1M in CH2C12, 55.1 mL, 55.1 mmol), and the mixture was stirred at-78 °C for 1.5 h. Aq. sat. tartaric acid monosodium monokalium salt in water (20 ml) was added and the mixture was allowed to warm up to rt. Water was added and the mixture was extracted with CH2C12. The org. extracts were dried over MgS04, filtered, and the solvents were removed under reduced pressure. Purification of the residue by FC yielded the title compound (4.4 g, 77percent). LC-MS: RT = 0.76 min; ES+ =156. 1.2-Chloro-3-methylpyridine-4-carbaldehyde (P) To the sol. of pyridine derivative O (9. 58 g, 36.7 mmol) in CH2C12 (190 mL) was at-78 °C added DIBAL (1M in CH2Cl2, 55.1 mL, 55.1 mmol), and the mixture was stirred at-78 °C for 1.5 h. Aq. sat. tartaric acid monosodium monokalium salt in water (20 ml) was added and the mixture was allowed to warm up to rt. Water was added and the mixture was extracted with CH2Cl2. The org. extracts were dried over MgS04, filtered, and the solvents were removed under reduced pressure. Purification of the residue by FC yielded the title compound (4.4 g, 77percent). LC-MS: RT = 0.76 min; ES+ = 156. 1.2-Chloro-3-methylpyridine-4-carbaldehyde (P); To the sol. of pyridine derivative O (9.58 g, 36.7 mmol) in CH2C12 (190 mL) was at-78 °C added DIBAL (1M in CH2C12, 55.1 mL, 55.1 mmol), and the mixture was stirred at-78 °C for 1.5 h. Aq. sat. tartaric acid monosodium monokalium salt in water (20 ml) was added and the mixture was allowed to warm up to rt. Water was added and the mixture was extracted with CH2C12. The org. extracts were dried over MgS04, filtered, and the solvents were removed under reduced pressure. Purification of the residue by FC yielded the title compound (4.4 g, 77percent). LC-MS: RT = 0.76 min; ES+ =156. 1.A mixture of methyl (R)-3 -(((R)- 1 -(1 H-indol-3 -yl)propan-2-yl)amino)-2-methylpropanoate(0.85 g, 3.1 mmol), To a sol. of 2-chloro-3, N-dimethyl-N-phenylisonicotinamide (124.9 g, 479 mmol) inCH2Cl2 (1300 mL) was added at -78 C DIBAL (1M in THF, 719 mL, 719 mmol) over 1h, and the mixture was stirred then for 2 h at this temperature. DIBAL (1M in THF, 281 mL, 281 mmol) was added again, and the reaction mixture was stirred at -60 C for 30 min. Aq. sat. potassium sodium tartrate (500 mL) was added over 30 min, the cooling bath was removed, and the mixture was stirred overnight at it. Water was added (100 mL), the org. phase was separated, and the water phase was extracted with CH2CI2 (2x100 mL). The combined org. phase were dried over MgSO4 filtered, and the solvents were removed under reduced pressure. Purification fy FC yielded the product (58.35 g, 78%) as pale yellow crystals.To a sol. of 2-chloro-3, A/-dimethyl-iV-phenylisonicotinamide (124.9 g, 479 mmol) in CH2CI2 (1300 mL) was added at -78 C DIBAL (1M in THF, 719 mL, 719 mmol) over 1 h, and the mixture was stirred for 2 h at this temperature. DIBAL (1M in THF, 281 mL, 281 mmol) was added again, and the reaction mixture was stirred at -60 C for 30 min. Aq. sat. potassium sodium tartrate (500 mL) was added over 30 min, the cooling bath was removed, and the mixture was stirred overnight at rt. Water was added (100 mL), the org. phase was separated, and thewater phase was extracted with CH2C12 (2x100 mL). The combined org. phases were dried over MgSO^ filtered, and the solvents were removed under reduced pressure. Purification by FC yielded the product (58.35 g, 78%) as pale yellow crystals.To the sol. of pyridine derivative O (9.58 g, 36.7 mmol) in CH2CI2 (190 mL) was at-78 C added DIBAL (1M in CH2C12, 55.1 mL, 55.1 mmol), and the mixture was stirred at-78 C for 1.5 h. Aq. sat. tartaric acid monosodium monokalium salt in water (20 ml) was added and the mixture was allowed to warm up to rt. Water was added and the mixture was extracted with CH2Cl2. The org. extracts were dried over MgS04, filtered, and the solvents were removed under reduced pressure. Purification of the residue by FC yielded the title compound (4.4 g, 77%). LC-MS: RT = 0.76 min; ES+ = 156.1.2-Chloro-3-methylpyridine-4-carbaldehyde (P); To the sol. of pyridine derivative O (9.58 g, 36.7 mmol) in CH2C12 (190 mL) was at-78 C added DIBAL (1M in CH2C12, 55.1 mL, 55.1 mmol), and the mixture was stirred at-78 C for 1.5 h. Aq. sat. tartaric acid monosodium monokalium salt in water (20 ml) was added and the mixture was allowed to warm up to rt. Water was added and the mixture was extracted with CH2C12. The org. extracts were dried over MgS04, filtered, and the solvents were removed under reduced pressure. Purification of the residue by FC yielded the title compound (4.4 g, 77%). LC-MS: RT = 0.76 min; ES+ = 156. 1To the sol. of pyridine derivative O (9.58 g, 36.7 mmol) in CH2C12 (190 mL) was at-78 C added DIBAL (1M in CH2C12, 55.1 mL, 55.1 mmol), and the mixture was stirred at-78 C for 1.5 h. Aq. sat. tartaric acid monosodium monokalium salt in water (20 ml) was added and the mixture was allowed to warm up to rt. Water was added and the mixture was extracted with CH2C12. The org. extracts were dried over MgS04, filtered, and the solvents were removed under reduced pressure. Purification of the residue by FC yielded the title compound (4.4 g, 77%). LC-MS: RT = 0.76 min; ES+ =156. 1.2-Chloro-3-methylpyridine-4-carbaldehyde (P) To the sol. of pyridine derivative O (9. 58 g, 36.7 mmol) in CH2C12 (190 mL) was at-78 C added DIBAL (1M in CH2Cl2, 55.1 mL, 55.1 mmol), and the mixture was stirred at-78 C for 1.5 h. Aq. sat. tartaric acid monosodium monokalium salt in water (20 ml) was added and the mixture was allowed to warm up to rt. Water was added and the mixture was extracted with CH2Cl2. The org. extracts were dried over MgS04, filtered, and the solvents were removed under reduced pressure. Purification of the residue by FC yielded the title compound (4.4 g, 77%). LC-MS: RT = 0.76 min; ES+ = 156. 1.2-Chloro-3-methylpyridine-4-carbaldehyde (P); To the sol. of pyridine derivative O (9.58 g, 36.7 mmol) in CH2C12 (190 mL) was at-78 C added DIBAL (1M in CH2C12, 55.1 mL, 55.1 mmol), and the mixture was stirred at-78 C for 1.5 h. Aq. sat. tartaric acid monosodium monokalium salt in water (20 ml) was added and the mixture was allowed to warm up to rt. Water was added and the mixture was extracted with CH2C12. The org. extracts were dried over MgS04, filtered, and the solvents were removed under reduced pressure. Purification of the residue by FC yielded the title compound (4.4 g, 77%). LC-MS: RT = 0.76 min; ES+ =156. 1.A sol. of aldehyde P (4.70 g, 30.2 mmol) and cyclopropylamine (4.20 ml, 60.4 mmol) in MeOH (65 mL) was stirred at rt for 4 h. NaBH4 (1.55 g, 39.2 mmol) was added and the mixture was stirred at rt for 12 h. Water and subsequently aq. 1M NaOH were added, and the solvents were partially removed under reduced pressure. The water phase was extracted with CH2Cl2 (2x). The combined org. extracts were dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Purification of the crude by FC yielded the title compound (4.66 g, 79%). LC-MS: RT = 0.43 min; ES+ = 197. 1.(2-Chloro-3-methylpyridin-4-ylmethyl)-cyclopropylamine (Q); A sol. of aldehyde P (4.70 g, 30.2 mmol) and cyclopropylamine (4.20 ml, 60.4 mmol) in MeOH (65 mL) was stirred at rt for 4 h. NaBH4 (1.55 g, 39.2 mmol) was added and the mixture was stirred at rt for 12 h. Water and subsequently aq. 1M NaOH were added, and the solvents were partially removed under reduced pressure. The water phase was extracted with CH2C12 (2x). The combined org. extracts were dried over MgS04, filtered, and the solvents were removed under reduced pressure. Purification of the crude by FC yielded the title compound (4.66 g, 79%). LC-MS: RT = 0.43 min; ES+ = 197. 1A sol. of aldehyde P (4.70 g, 30.2 mmol) and cyclopropylamine (4.20 ml, 60.4 mmol) in MeOH (65 mL) was stirred at rt for 4 h. NaBH4 (1.55 g, 39.2 mmol) was added and the mixture was stirred at rt for 12 h. Water and subsequently aq. 1M NaOH were added, and the solvents were partially removed under reduced pressure. The water phase was extracted with CH2C12 (2x). The combined org. extracts were dried over MgS04, filtered, and the solvents were removed under reduced pressure. Purification of the crude by FC yielded the title compound (4. 66 g, 79%). LC-MS: RT = 0.43 min; ES+ = 197. 1.(2-Chloro-3-methylpyridin-4-ylmethyl)-cyclopropylamine (Q) A sol. of aldehyde P (4.70 g, 30.2 mmol) and cyclopropylamine (4.20 ml, 60.4 mmol) in MeOH (65 mL) was stirred at rt for 4 h. NaBH4 (1.55 g, 39.2 mmol) was added and the mixture was stirred at rt for 12 h. Water and subsequently aq. 1M NaOH were added, and the solvents were partially removed under reduced pressure. The water phase was extracted with CHUCK (2x). The combined org. extracts were dried over MgS04, filtered, and the solvents were removed under reduced pressure. Purification of the crude by FC yielded the title compound (4.66 g, 79%). LC-MS: RT = 0.43 min; ES+ =197. 1.(2-Chloro-3-methylpyridin-4-ylmethyl)-cyclopropylamine (Q); A sol. of aldehyde P (4.70 g, 30.2 mmol) and cyclopropylamine (4.20 ml, 60.4 mmol) in MeOH (65 mL) was stirred at rt for 4 h. NaBH4 (1.55 g, 39.2 mmol) was added and the mixture was stirred at rt for 12 h. Water and subsequently aq. 1M NaOH were added, and the solvents were partially removed under reduced pressure. The water phase was extracted with CH2C12 (2x). The combined org. extracts were dried over MgS04, filtered, and the solvents were removed under reduced pressure. Purification of the crude by FC yielded the title compound (4.66 g, 79%). LC-MS: RT = 0.43 min; ES+ = 197. 1.A mixture of A mixture of

Molecular Weight:155.58
XLogP3:1.6
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:1
Exact Mass:155.0137915
Monoisotopic Mass:155.0137915
Topological Polar Surface Area:30
Heavy Atom Count:10
Complexity:129
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes