Hydrochloric Acid → HCID 66967622, compound

Participants

Reaction Conditions

Reaction Steps

A propionitrile (15 mL) solution of 2-amino-5-bromo-nicotinonitrile (198 mg, 1 mmol), N-methyl-N-(1-methyl-1H-indol-2-ylmethyl)-acrylamide (457 mg, 2 mmol) and diisopropyl-ethylamine (523 μL, 3 mmol) was purged with Argon for 10 min. Pd(OAc)2 (23 mg, 0.1 mmol) and P(o-Tol)3 (61 mg, 0.2 mmol) was added and the Argon purge was repeated. The mixture was heated to 100° C. and stirred for 6 hr under Argon. Upon cooling, solvents were removed under vacuo and the residue was purified by Flash chromatography (silica, 2% MeOH in CH2Cl2). The purified free base was converted to its HCl salt by addition of HCl (1 mL, 1 mmol, IM in ether). The salt was washed with ether and dried to afford 162 mg (43%) of the title compound. 1H NMR (300 MHz, DMSO-d6) δ 8.50 (m, 2H), 7.55-6.95 (m, 4H), 6.40 and 6.17 (rotamers, 2s, 1H), 5.03 and 4.83 (rotamers, 2s, 2H), 3.71 and 3.67 (rotamers, 2s, 3H), 3.09 and 2.96 (rotamers, 2s, 3H). MS (ESI) m/e: 346.1662 (M+H)+.

Provenance & Evidence