反应详情

To a solution of 2-(4-Bromophenyl)-N-butyl-3-[2-(butylamino)-4-pyrimidinyl]pyrazolo-[1,5-a]pyridin-7-amine (52 mg, 0.11 mmol) in tetrahydrofuran was added phenylboronic acid (26 mg, 0.21 mmol), sodium carbonate (0.21 mL, 2 M aqueous, 0.42 mmol), and dichlorobistriphenylphosphine palladium (II) (7.5 mg, 0.01 mmol). The mixture was heated at reflux for 3.5 hours. The resultant solution was cooled to room temperature and diluted with ether and water was added. The organic layer was washed with brine. The aqueous layer was extracted with ether and the combined organics dried over magnesium sulfate. Filtration and concentration followed by flash chromatography provided 2-[1,1′-biphenyl]-4-yl-N-butyl-3-[2-(butylamino)-4-pyrimidinyl]pyrazolo[1,5-a]pyridin-7-amine (37 mg, 73%) as a yellow solid. 1H NMR (CDCl3): δ 8.05 (d, 1 H), 7.83–7.69 (m, 7 H), 7.51 (m, 2 H), 7.43–7.33 (m, 2 H), 6.44 (d, 1 H), 6.12 (t, 1 H), 6.05 (d, 1 H), 5.16 (broad, 1 H), 3.52 (m, 2 H), 3.42 (m, 2 H), 1.84–1.43 (m, 8 H), 1.05–0.99 (m, 6 H); MS m/z 491 (M+1).

1. temperatureThe mixture was heated
2. temperatureat reflux for 3.5 hours
3. additionwas added
4. washThe organic layer was washed with brine
5. extractionThe aqueous layer was extracted with ether
6. dry with materialthe combined organics dried over magnesium sulfate
7. filtrationFiltration and concentration