174610-11-8

Step c: Synthesis of N-(1H-pyrrolo[2,3-c]pyridin-5-yl)acetamide (Z)-N-[4-[2-(dimethylamino)vinyl]-5-nitro-2-pyridinyl]acetamide (0.7 g, 3 mmol, product of step b) was dissolved in a mixed solvent of methanol and dichloromethane (5:1, 120 mL) and carbon-loaded palladium (0.4 g) and acetic acid (7 mL) were added. After displacing the air in the reaction system with hydrogen, the reaction mixture was stirred at room temperature overnight. Upon completion of the reaction, the reaction mixture was filtered through a bed of diatomaceous earth and the filtrate was washed with methanol (100 mL). The filtrates were combined and concentrated under reduced pressure, and the resulting crude product was purified by silica gel column chromatography (eluent: methanol/dichloromethane, 2%) to afford N-(1H-pyrrolo[2,3-c]pyridin-5-yl)acetamide (0.35 g, 71% yield). 1H NMR (400 MHz, DMSO-d6): δ 11.43 (br.s, 1H), 10.13 (s, 1H), 8.46 (s, 1H), 8.21 (s, 1H), 7.56 (t, J = 2.76 Hz, 1H), 6.45 (t, J = 1.88 Hz, 1H), 2.06 (s, 3H). MS: 176.44 (M + 1).

[1] Patent: WO2012/160464, 2012, A1. Location in patent: Page/Page column 63-64
[2] Patent: US2014/155398, 2014, A1. Location in patent: Paragraph 0389