反应详情

温度

120 °C

Compound [5] was prepared as follows. 3-(1,3-benzoxazol-2-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine (150 mg), 1-(5-bromothiazol-2-yl)-4-methyl-piperazine (117 mg), bis(triphenylphosphine) palladium (II) chloride (15.61 mg) and caesium fluoride (169 mg) were weighed out in a microwave vial and sealed. Methanol (1.5 ml) was added and argon was bubbled in the resulting suspension for 10 minutes. The resulting mixture was heated in the 300 W microwave at 120° C. for 20 minutes. The crude product was purified by flash chromatography on silica gel eluting with 0 to 3% methanol in dichloromethane then 3% to 5% methanolic ammonia 7N in dichloromethane. The solvent was evaporated to dryness to afford the product, which was stirred at room temperature for 1 h in acetonitrile (3 ml), collected by filtration, washed with acetonitrile and dried under vacuum at 40° C., to give 3-(1,3-benzoxazol-2-yl)-5-[2-(4-methylpiperazin-1-yl)thiazol-5-yl]pyridin-2-amine (80 mg). NMR Spectrum: (CDCl3) 2.39 (s, 3H), 2.54-2.65 (m, 4H), 3.56-3.65 (m, 4H), 6.96 (m, 2H), 7.35 (s, 1H), 7.36-7.40 (m, 2H), 7.61 (dd, 1H), 7.74 (dd, 1H), 8.31-8.35 (m, 2H); Mass spectrum: M+H+ 393. There was no deprotection step.

1. customsealed
2. customargon was bubbled in the resulting suspension for 10 minutes
3. customThe crude product was purified by flash chromatography on silica gel eluting with 0 to 3% methanol in dichloromethane
4. customThe solvent was evaporated to dryness
5. customto afford the product, which
6. filtrationcollected by filtration
7. washwashed with acetonitrile
8. customdried under vacuum at 40° C.