Methyl 4-methylnicotinate

4-Methyl-nicotinic acid methyl esterTrieithylamine (45 g, 0.45 mol) was added into the mixture of compound 3-bromo-4-methyl-pyridine (25 g, 0.15 mol), Pd(OAc)2 (3.37 g, 0.015 mol) and dppf (6.19 g, 0.015 mol) in DMF/MeOH (150 mL/150 mL) dropwise. A metal reactor was charged with 3-bromo-4-methyl-pyridine (200 g, 0.116 mol) and a mixture of DMF/MeOH (1 L/1L). To this was added EtProcedure b: A metal reactor was charged with 3-bromo-4-methyl-pyridine (200 g, 0.116 mol) and a mixture of DMF/MeOH (1 L/1L). To this was added EtProcedure b: A metal reactor was charged with 3-bromo-4-methyl-pyridine (200 g, 0.1 16 mol) and a mixture of DMF/MeOH (1 L/1L). To this was added EtA metal reactor was charged with 3-bromo-4-methyl-pyridine (200 g, 0.116 mol) and a mixture of DMF/MeOH (1 L/1L). To this was added Et3N (400 g, 0.395 mol), palladium (II) acetate (8 g, 0.036 mol) and 1, 1’-bis(diphenylphosphino)ferrocene (16 g, 0.029 mol). The reactor was closed and pressurized with CO gas (3 MPa) and the reaction mixture was stirred and heated overnight at 140 °C. The RM was cooled, filtered and concentrated in vacuo. The residue was purified by flash column chromatography over silica gel (gradient eluent:EtOAc/Petroleum ether from 1/1 to 1/0). The product fractions were collected and the solvent was evaporated to afford the desired intermediate 1 (90 g, 5 1percent).Procedure b: A metal reactor was charged with 3-bromo-4-methyl-pyridine (200 g, 0.116 mol) and a mixture of DMF/MeOH (1 L/1L). To this EtA solution of 4-methylnicotinic acid (2.00 g, 14.6 mmol) and concentrated HGeneral procedure: To a solution of carboxylic acid 22 or 29–31 (0.1mol) in dry methanol (150mL), concd H4-Methyl-3-pyridinecarboxylic acid hydrochloride (1 : 1) (40 g, 230.4 mmol) was added to a refluxing mixture of sulphuric acid (20 mL) and MeOH (400 mL). The mixture was re fluxed overnight, then it was evaporated and the resulting slurry was added to a cold solution of NaHCOs (64 g) in water (360 mL). The product was extracted with DCM and the organic layer was dried over MgSC^, filtered and evaporated, yielding intermediate 1 (28.70 g, 83percent).Procedure a: 4-Methyl-3-pyridinecarboxylic acid hydrochloride (1 : 1) (40 g, 230.4 mmol) was added to a refluxing mixture of sulphuric acid (20 mL) and MeOH (400 mL). The mixture was refluxed overnight, then it was evaporated and the resulting slurry was added to a cold solution of NaHC0Procedure a: 4-Methyl-3-pyridinecarboxylic acid hydrochloride (1 : 1) (40 g, 230.4 mmol) was added to a refluxing mixture of sulphuric acid (20 mL) and MeOH (400 mL). The mixture was refluxed overnight, then it was evaporated and the resulting slurry was added to a cold solution of NaHC04-Methyl-3-pyridinecarboxylic acid hydrochloride (1:1) (40 g, 230.4mmol) was added to a refluxing mixture of sulphuric acid (20 mL) and MeOH (400mL). The mixture was refluxed overnight, then it was evaporated and the resulting slurry was added to a cold solution of NaHCO3 (64 g) in water (360 mL). The product was extracted with DCM and the OL was dried over MgSO4, filtered and evaporated, yielding intermediate 1 (28.70 g, 83percent).4-Methyl-3-pyridinecarboxylic acid hydrochloride (1:1) (40 g, 230.4 mmol) was added to a refluxing mixture of sulphuric acid (20 mL) and MeOH (400mL). The mixture was refluxed overnight, then it was evaporated and the resulting slurry was added to a cold solution of NaHCO3 (64 g) in water (360 mL). The product was extracted with DCM and the OL was dried over MgSO4, filtered and evaporated, yielding intermediate 21(28.70 g, 83percent)Collection A: Preparation of 4-Me-101A 500-mL, three-neck, round-bottomed flask was charged with 4-methylnicotinic acid hydrochloride (7.4 g, 42.8 mmol) and hydrochloric acid in methanol (200 mL; 200 mg/mL). The mixture was heated at a gentle reflux for 5 h, then it was stirred for 16 h, while cooling to ambient temperature. An in-process HPLC was run after stirring for 15 h at ambient temperature [HPLC (Method A): 95.0percent (AUC), t

Molecular Weight:151.16
XLogP3:1.1
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:2
Exact Mass:151.063328530
Monoisotopic Mass:151.063328530
Topological Polar Surface Area:39.2
Heavy Atom Count:11
Complexity:147
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes