Cesium carbonate → Tert-butyl 3-(2-[[7-(pentafluoroethyl)isoquinolin-1-yl]amino]acetamido)azetidine-1-carboxylate

Participants

Reaction Conditions

Reaction Steps

Into a 8 mL sealed tube, was placed 1-chloro-7-(pentafluoroethyl)isoquinoline (as prepared in the previous step, 282 mg, 1.00 mmol, 1.00 equiv), tert-butyl 3-(2-aminoacetamido)azetidine-1-carboxylate (prepared as described in Example 1, Step E) (250 mg, 1.09 mmol, 1.09 equiv), Cs2CO3 (1.0 g, 3.07 mmol, 3.06 equiv), BINAP (24 mg, 0.04 mmol, 0.04 equiv), Pd(OAc)2 (10 mg, 0.04 mmol, 0.04 equiv) and tol (2 mL). The reaction mixture was stirred overnight at 120° C. The resulting mixture was concentrated under vacuum. The residue was purified by chromatography over a silica gel column with dichloromethane/methanol (10:1). This resulted in 0.12 g (25%) of tert-butyl 3-(2-[[7-(pentafluoroethyl)isoquinolin-1-yl]amino]acetamido)azetidine-1-carboxylate as a brown solid.

Provenance & Evidence