Dimethylformamide → HCID 10183232, compound

Participants

Reaction Steps

To a solution of 2-(3-bromophenyl)-N-cyclopentyl-3-[2-(cyclopentylamino)-4-pyrimidinyl]pyrazolo[1,5-a]pyridin-7-amine (500 mg, 0.97 mmol) in N,N-dimethylformamide (25 mL) was added zinc cyanide (68 mg, 0.58 mmol), tris(dibenzylidineacetone)bipalladium(0) (888 mg, 0.97 mmol) and 1,1′-bis(diphenylphosphino) ferrocene (1.29 g, 2.3 mmol). The resultant mixture was heated at 120° C. for 20 hours. After cooling to room temperature, ethyl acetate was added to the reaction mixture. The organic phase was washed with water, brine and dried over magnesium sulfate. Filtration and concentration, followed by purification with flash chromatography (40:60 ethyl acetate:hexanes) gave 3-{7-(cyclopentylamino)-3-[2-(cyclopentylamino)-4-pyrimidinyl]pyrazolo[1,5-a]pyridin-2-yl}benzonitrile (0.19 g, yield 42%) as a yellow foam. 1H NMR (CDCl3): δ 8.07 (m, 2H), 7.89 (d, 1H), 7.70 (d, 1H), 7.62 (d, 1H), 7.52 (t, 1H), 7.33 (t, 1H), 6.33 (d, 1H), 6.06 (d, 1H), 6.00 (d, 1H), 5.16 (d, 1H), 4.25 (m, 1H), 4.02 (m, 1H), 2.15 (m, 2H), 2.03 (m, 2H), 1.85–1.51 (m, 12H). MS m/z 464 (M+1).

Provenance & Evidence