反应详情

温度

100 °C

To a solution of 2-(3-bromophenyl)-N-cyclopentyl-3-[2-(cyclopentylamino)-4-pyrimidinyl]pyrazolo[1,5-a]pyridin-7-amine (100 mg, 0.19 mmol) in dimethylformamide (6 mL) was added phenylboronic acid (47 mg, 0.39 mmol), palladium (II) acetate (4.3 mg, 0.02 mmol), potassium carbonate (54 mg, 0.39 mmol) and triphenyl phosphine (30 mg, 0.08 mmol). The reaction was heated at 100° C. for 24 hours. After allowing the reaction mixture to cool to room temperature, ethyl acetate and water were added. The organic layer was separated and washed with water, then brine and dried (magnesium sulfate). Filtration and concentration, followed by purification with flash chromatography (4:6 ethyl acetate:hexanes) gave 2-[1,1′-biphenyl]-3-yl-N-cyclopentyl-3-[2-(cyclopentylamino)-4-pyrimidinyl]pyrazolo[1,5-a]pyridin-7-amine as a yellow foam (87 mg, 89%). 1H NMR (CDCl3): δ 8.01 (d, 1H), 7.92 (s, 1H), 7.81 (d, 1H), 7.69–7.62 (m, 4H), 7.53 (t, 1H), 7.47–7.43 (m, 2H), 7.38–7.32 (m, 2H), 6.40 (d, 1H), 6.09–6.05 (m, 2H), 5.16 (m, 1H), 4.37 (m, 1H), 4.03 (m, 1H), 2.15–2.06 (m, 4H), 1.82–1.64 (m, 12H); MS m/z 515 (M+1).

1. temperatureto cool to room temperature
2. customThe organic layer was separated
3. washwashed with water
4. dry with materialbrine and dried (magnesium sulfate)
5. filtrationFiltration and concentration
6. customfollowed by purification with flash chromatography (4:6 ethyl acetate:hexanes)