(3-bromo-2-fluorophenyl)methanamine hydrochloride

To a stirred solution of (£, Z)-3-bromo-2-fluorobenzaldehyde O-methyl oxime (1 .0 g, 4.31 mmol, 1 equiv) in THF (10 mL) was added borane dimethyl sulfide complex (4 mL, 43.10 mmol, 10 equiv) at 0 C, and the mixture was then stirred at 80 C for 5 h. After consumption of the starting material, the reaction mixture was cooled to 0 C, and quenched with methanol dropwise. 20% HCI in dioxane (5 mL) was added to this reaction mixture, which was then stirred at 90C for 1 h. The reaction mixture was evaporated under vacuum to obtain solid product. The solid product was triturated with n-pentane (10 mL)and ether (10 mL) to obtained (3-bromo-2-fluorophenyl)methanamine hydrochloride as off white solid (0.9g, 87%). LC-MS (ES) m/z = 204.0, 206.0 [M+H]+. NMR (400 MHz, DMSO-d6) delta ppm 4.07 (s, 2 H), 7.21 (t, J = 8 Hz, 1 H), 7.58 (s, 1 H), 7.67 - 7.74 (m, 1 H), 8.47 (br.s, 3 H). Run2: To a stirred solution of (£, Z)-3-bromo-2-fluorobenzaldehyde O-methyl oxime (14.3 g, 61 .63 mmol, 1 equiv) in THF (150 mL) was added borane dimethyl sulfide complex (58 mL, 616.37 mmol, 10 equiv) at 0 C, and stirred at 80 C for 5 h. After consumption of the starting material the reaction mixture was cooled to 0 C, quenched with methanol dropwise. 20% HCI in dioxane (50 mL) was added to the reaction mixture, and it was then stirred at 90C for 1 h. The reaction mixture was evaporated in vacuo to obtain solid product. The solid product was triturated with n-pentane (50 mL) and ether (50 mL) to obtained (3-bromo- 2-fluorophenyl)methanamine hydrochloride as an offwhite solid (14.2g, 96%). LC-MS (ES) m/z = 204.0, 206.0 [M+H]+. NMR (400 MHz, DMSO-d6) delta ppm 4.06 (s, 2 H), 7.20 (t, J = 7.6 Hz, 1 H), 7.60 (t, J = 7.2 Hz, 1 H), 7.71 (t, J = 7.2 Hz, 1 H), 8.59 (br.s, 3 H).To a stirred solution of A mixture of 3-bromo-2-fluoro-benzonitrile (1.0 g, 5.0 mmol) and Raney-Ni in EtOH (4% NH3) (30 mL) was stirred under a hydrogen atmosphere (1 atm) at RT for 6.5 h. The reaction mixture was filtered through Celite, rinsed down with CH2CI2, and the filtrate was concentrated under reduced pressure. The crude mixture was taken up in 1 M aqueous HCI, the organic layer was separated, and the water phase was freeze-dried overnight to afford the title compound as a white solid. MS (LC/MS): 206.0 [M+H]+; tR (HPLC conditions c): 2.21 min.Example 175 N-[(3-Bromo-2-fluorophenyl)methyl]-N'-{[1, 6-diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3, 4-b]pyridin-5-yl]methyl}-1, 3-benzenedicarboxamide A mixture of 3-[({[1, 6-diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3, 4-b]pyridin-5-yl]methyl}amino)carbonyl]benzoic acid (210 mg, 0.466 mmol),

Molecular Weight:240.50
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:1
Exact Mass:238.95127
Monoisotopic Mass:238.95127
Topological Polar Surface Area:26
Heavy Atom Count:11
Complexity:110
Covalently-Bonded Unit Count:2
Compound Is Canonicalized:Yes