Chloroacetone → 1H-Pyrazolo(4,3-b)pyridine

Participants

Reaction Steps

Using a procedure similar to that described in Example 1, except using 2-amino-2-methyl-3-(2H-pyrazolo[4,3-b]pyridin-2-yl)-propionitrile (27 mg), the title compound was isolated as a white solid (8 mg). MS (ES): M/Z [M+H]=390. 1H NMR: (400 MHz, CHLOROFORM-d): 1.94 (s, 3H), 4.87 (d, J=14.1 Hz, 1H), 5.04 (d, J=14.1 Hz, 1H), 7.31 (d, J=7.6 Hz, 3H), 7.90 (d, J=8.8 Hz, 2H), 8.05 (d, J=8.8 Hz, 1H), 8.30 (s, 1H), 8.43 (s, 1H) and 8.65 (d, J=2.9 Hz, 1H). 19F NMR (376 MHz, CHLOROFORM-d): −58.1 (s, 3F). 2-Amino-2-methyl-3-(2H-pyrazolo[4,3-b]pyridin-2-yl)-propionitrile (37 mg) was prepared using a procedure similar to that described in Example 1, part b, except starting from 1-(2H-pyrazolo[4,3-b]pyridin-2-yl)propan-2-one (37 mg). 1-(2H-Pyrazolo[4,3-b]pyridin-2-yl)propan-2-one (37 mg, 6.6%; MS (ES): M/Z [M+H]=176) was prepared using a procedure similar to that described in Example 182 part g using chloroacetone and potassium carbonate except starting from 1H-pyrazolo[4,3-b]pyridine (380 mg). 1H-pyrazolo[4,3-b]pyridine (380 mg, 34%) was prepared using a procedure similar to that described in Example 182 part f except starting from 3-amino-2-methylpyridine (1 g).

Provenance & Evidence