反应详情

To a mixture of 7-(2-chlorophenyl)-8-iodo-2-methyl-3H-pyrazolo-[1,5-a][1,3,5]triazin-4-one (I-1A-1d; 141 g, 364 mmol) and 4-chlorophenylboronic acid (85.1 g, 544 mmol) in dimethoxyethane (1.4 L) was added 2 M aqueous Na2CO3 (365 ml) and then (1,1′-bis(diphenylphosphino)ferrocene)-dichloropalladium(II), dichloromethane complex (5.80 g, 7.17 mmol). The reaction was heated at reflux for 16 hours, cooled, and the organic layer separated and then concentrated under reduced pressure. The residue was dissolved in methyltetrahydrofuran (1.4 L) and washed with 1 M aqueous NaOH (2×700 ml) and 1 M aqueous HCl (700 ml). The solvent was removed, in vacuo, to give a brown solid which was suspendend in methanol (1.2 L). The mixture was concentrated to one-third volume, the solids were collected by vacuum filtration in a course sintered glass funnel, washed with methanol (1 L) and then dried, in vacuo, to afford product I-2A-1a as a light-brown solid (103 g, 76%): +APcI MS (M+1) 371.3; 1H NMR (400 MHz, DMSO-d6) δ 12.73 (s, 1H), 7.54-7.43 (m, 4H), 7.35-7.26 (m, 4H), 2.35 (s, 3H).

1. temperatureThe reaction was heated
2. temperatureat reflux for 16 hours
3. temperaturecooled
4. customthe organic layer separated
5. concentrationconcentrated under reduced pressure
6. dissolutionThe residue was dissolved in methyltetrahydrofuran (1.4 L)
7. washwashed with 1 M aqueous NaOH (2×700 ml) and 1 M aqueous HCl (700 ml)
8. customThe solvent was removed, in vacuo
9. customto give a brown solid which
10. concentrationThe mixture was concentrated to one-third volume
11. filtrationthe solids were collected by vacuum filtration in a course sintered glass funnel
12. washwashed with methanol (1 L)
13. customdried, in vacuo
14. customto afford product