Dichloromethane → HCID 59540521, compound

Participants

Reaction Steps

A mixture of 1-(2-bromo-5H-pyrrolo[2,3-b]pyrazin-7-yl)-2,2-dimethyl-propan-1-one (50 mg, 0.18 mmol), 1-[2-methoxy-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-pyrrolidine (60 mg, 0.2 mmol), potassium carbonate (63 mg, 0.46 mmol), Pd(dppf)Cl2.CH2Cl2 (11 mg, 0.013 mmol), 1.4 mL dioxane and 0.3 mL water was stirred at 150° C. in a microwave for 30 min. The resulting mixture was treated with additional Pd(dppf)Cl2.CH2Cl2 (2 mg, 0.002 mmol), stirred at 160° C. in a microwave for 10 min, and partitioned between ethyl acetate and water. The combined organic layers were dried over Na2SO4 and concentrated to give a dark brown residue. The crude product was purified by preparative thin layer chromatography using 140:9.5:0.5 CH2Cl2:MeOH:conc NH4OH as eluant. The resultant brown solid was washed with CH2Cl2 and ethyl ether to provide 20 mg (29%) of 1-[2-(4-methoxy-3-pyrrolidin-1-yl-phenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-2,2-dimethyl-propan-1-one as a yellow solid. MP 211-213° C., M+H 379.

Provenance & Evidence