Dichloromethane → methyl 1-[3-(benzyloxy)propyl]-4-[5-({2-[(4-{[ethoxy(hydroxy)phosphoryl]methyl}-2-methoxyphenyl)amino]-5-(trifluoromethyl)pyrimidin-4-yl}amino)-6-(methylcarbamoyl)pyridin-2-yl]-1H-pyrrole-2-carboxylate

Participants

Reaction Steps

A mixture of [1,1′-Bis(diphenylphosphino)ferrocene]dichloropalladium(II), complex with dichloromethane (1:1) (77.9 mg, 0.095 mmol), potassium carbonate (366 mg, 2.65 mmol), ethyl hydrogen (4-{[4-{[6-bromo-2-(methylcarbamoyl)pyridin-3-yl]amino}-5-(trifluoromethyl)pyrimidin-2-yl]amino}-3-methoxybenzyl)phosphonate (Compound 38C, 543 mg, 0.877 mmol) and methyl 1-[3-(benzyloxy)propyl]-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrole-2-carboxylate (Compound 38E, 385 mg, 0.964 mmol) in 4:1 dioxane:H2O (3.8 mL) was degassed with Argon and irradiated for 30 min at 100° C. in a CEM microwave reactor. The reaction was then concentrated in vacuo and purified using a Teledyne ISCO Combiflash® Rf system [5→100% MeOH in Water] to afford 586 mg of the title compound (82%). MS (ESI): m/z 812.60 [M+H]+. UPLC: tR=1.57 min (UPLC-TOF: polar—2 min).

Provenance & Evidence