反应详情
EQUATION
反应方程式
REACTANTS
反应物
PRODUCTS
生成物
AUXILIARIES
试剂、催化剂与溶剂
CONDITIONS
反应条件
- 温度
- 100 °C
PROCEDURE
实验过程
Diethyl [4-({4-[(7-bromo-2-methyl-3-oxo-2,3-dihydro-1H-isoindol-4-yl)amino]-5-(trifluoromethyl)pyrimidin-2-yl}amino)-3-methoxybenzyl]phosphonate (20.0 mg, 0.0304 mmol), 4-(Dihydroxyboryl)benzoic acid (10.1 mg, 0.0608 mmol), potassium carbonate (12.6 mg, 0.0911 mmol), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II), complex with dichloromethane (1:1) (2.48 mg, 0.00304 mmol), 1,4-dioxane (0.6 mL) and water (0.15 mL) were mixed and heated in microwave at 100° C. for 30 minutes. The crude mixture was passed through Thiol-SPE cartridge to remove Pd and was subsequently purified by MDP to obtain the title compound (5.7 mg, 27% yield). 1H NMR (400 MHz, DMSO-d6) δ=1.13 (t, J=7.1 Hz, 6 H), 3.08 (s, 3 H), 3.34 (d, J=21.5 Hz, 2 H), 3.75 (s, 3 H), 3.85-4.02 (m, 4 H), 4.67 (s, 2 H), 6.94 (d, J=8.1 Hz, 1 H), 7.08 (br. s., 1 H), 7.43 (br. s., 1 H), 7.58 (d, J=8.6 Hz, 1 H), 7.75 (m, J=8.3 Hz, 2 H), 8.02 (m, J=8.6 Hz, 2 H), 8.42 (s, 1 H), 9.20 (s, 1 H), 13.05 (s, 1 H). MS (ES+): m/z 700.25 (100) [MH+]; HPLC: tR=1.07 min (UPLC, purity).
WORKUP
后处理
- customto remove Pd
- customwas subsequently purified by MDP