Cesium carbonate → Tert-butyl 3-(2-(7-(trifluoromethyl)isoquinolin-1-ylamino)acetamido)azetidine-1-carboxylate

Participants

Reaction Conditions

Reaction Steps

Into a 8 mL sealed tube, was placed 1-chloro-7-(trifluoromethyl)isoquinoline (as prepared in the previous step, 433 mg, 1.87 mmol, 1.00 equiv), tert-butyl 3-(2-aminoacetamido)azetidine-1-carboxylate (prepared as described in Example 1, Step E) (460 mg, 2.01 mmol, 1.18 equiv), Pd(OAc)2 (15 mg, 0.07 mmol, 0.05 equiv), Cs2CO3 (1500 mg, 4.60 mmol, 1.77 equiv), BINAP (30 mg, 0.05 mmol, 0.04 equiv) and toluene (2 mL). The reaction mixture was stirred for 12 h at 100° C. in an oil bath. The solids were filtered off. The resulting mixture was concentrated under vacuum. The residue was purified by chromatography over a silica gel column with ethyl acetate:retroleum ether (1:3). The title compound was obtained as an off white solid.

Provenance & Evidence