Dichloromethane → 6-(2,4-Dichloro-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-2-methylbenzo[d]oxazole

Participants

Reaction Conditions

Reaction Steps

To a solution of 2,4-dichloro-5-iodo-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine (1 equiv), 2-methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[d]oxazole (1 equiv), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II), complex with DCM (0.1 equiv) in a 3:1 mixture of 1,4-dioxane and water (0.2 M) was added sodium carbonate (3 equiv). The reaction was stirred at 85° C. for 15 h. The reaction mixture was quenched with saturated aqueous sodium chloride and then extracted with ethyl acetate. The organic phase was combined and washed with saturated aqueous sodium chloride. The organic layer was dried (magnesium sulfate), filtered, and concentrated. The crude was purified by silica gel column chromatography (0-50% ethyl acetate in hexane) to give the title compound (72.0% yield) as a brown oil 1H NMR (400 MHz, DMSO-d6) δ ppm −0.06 (s, 9H) 0.83-0.92 (m, 2H) 2.64 (s, 3H) 3.55-3.65 (m, 2H) 5.65 (s, 2H) 7.47 (dd, J=8.00, 1.76 Hz, 1H) 7.72 (d, J=8.20 Hz, 1H) 7.79-7.83 (m, 1H) 8.05 (s, 1H); MS (ESI) m/z 449.5 [M+1]+.

Provenance & Evidence