3-bromo-1H-pyrazolo[4,3-b]pyridine

General procedure: To a stirred solution of 3-bromo-1 H-pyrazolo[4, 3-b]pyridine (500 mg, 2.52 mmol) in DMF, NaH (60%) (201 mg, 5.04 mmol) was added at 0C and it was stirred for 15min. Then, 1 -bromo-2-methoxyethane (420 mg, 3.02 mmol) was added and the reaction mixture was stirred at rt for 2h. The reaction mixture was quenched with water and extracted with EtOAc. The organic layer was dried over anhydrous Na2S04, and it was concentrated under reduced pressure. The crude compound was purified by flash column chromatography on 230-400 silica using 45% EtOAc in pet ether as an eluent to afford the title compound (430 mg, 66%) as a gummy solid.To a stirred solution of 3-bromo-1 H-pyrazolo[4, 3-b]pyridine (500 mg, 2.52 mmol) in DMF, NaH (60%) (201 mg, 5.04 mmol) was added at 0C and it was stirred for 15min. Then, 1 -bromo-2-methoxyethane (420 mg, 3.02 mmol) was added and the reaction mixture was stirred at rt for 2h. The reaction mixture was quenched with water and extracted with EtOAc. The organic layer was dried over anhydrous Na2S04, and it was concentrated under reduced pressure. The crude compound was purified by flash column chromatography on 230-400 silica using 45% EtOAc in pet ether as an eluent to afford the title compound (430 mg, 66%) as a gummy solid.LC-MS (method 24): R, = 2.63 min; m/z = 258.01 (M+2H+), To a stirred solution of 3-bromo-1 W-pyrazolo[4, 3-b]pyridine (800 mg, 4.03 mmol), in acetonitrile (10 mL) CS2CO3 (3940 mg, 12, 09 mmol), 2-(2-chloroethyl)-1-methyl-1H-imidazole (640 mg, 4.43 mmol) and Nal (303 mg, 2.02 mmol), were added at RT. The reaction mixture was heated at 90C overnight. The crude reaction was filtered through a celite pad, washed with EtOAc (50 mL), and the solution was evaporated to dryness. The crude compound was purified twice by column chromatography reverse phase with 10mM Ammonium acetate/Acetonitrile to afford to afford the title compound (430 mg, 35%) as a gummy solid.LC-MS (method 26): R, = 1.99 min; m/z = 306.0 (M+H+).To a stirred solution of 3-bromo-1 H-pyrazolo[4, 3-b]pyridine (200 mg, 1.01 mmol) in DMF (5 mL), 3, 4-dihydro- 2H-pyran (127 mg, 1.51 mmol) and a catalytic amount of pTSA were added at rt. The resulting solution was stirred at 85 C for 24h. The reaction was cooled to rt, diluted with water and extracted with EtOAc. The organic layer was washed with water and brine solution, dried over anhydrous Na2SC>4, and filtered. The resulting solution was concentrated under reduced pressure to get crude a residue that was purified by flash columnchromatography to afford the title compound (150 mg, 52.8 %).LC-MS (method 1): Rt = 2.24 min; m/z = 282.30 (M+H+).i) Preparation of methyl 3-fluoro-4-(1H-pyrazolo[4, 3-b]pyridin-3-yl)benzoate (B-2) A mixture of To a solution of

Molecular Weight:198.02
XLogP3:1.6
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Exact Mass:196.95886
Monoisotopic Mass:196.95886
Topological Polar Surface Area:41.6
Heavy Atom Count:10
Complexity:130
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes