2-Methylpropan-2-olate → HCID 89647581, compound

Participants

Reaction Steps

A reaction mixture of 5-Bromo-quinoline-8-carbonitrile (200.00 mg; 0.86 mmol; 1.00 eq), (3-amino-4-(3-trifluoromethoxy-phenyl)-pyrrolidine-1-carboxylic acid tert-butyl ester (0.41 ml; 1.03 mmol; 1.20 eq.) (trans_racemic), sodium; 2-methyl-propan-2-olate (181.43 mg; 1.89 mmol; 2.20 eq.), and dicyclohexyl-(2′,4′,6′-triisopropyl-biphenyl-2-yl)-phosphane (122.73 mg; 0.26 mmol; 0.30 eq.) in toluene (5 ml) in microwave tube was degas, followed by adding Pd2(dba)3 (74.02 mg; 0.13 mmol; 0.15 eq.). The resulting mixture was stirred for 10 min at RT, placed in microwave at 100° C. for 20 min. The reaction mixture was concentrated and re-dissolved in DMSO, purified by prep HPLC (Basic condition, 70-75% acetonitrile in water) to give 3-(8-cyano-quinolin-5-ylamino)-4-(3-trifluoromethoxy-phenyl)-pyrrolidine-1-carboxylic acid tert-butyl ester (trans_racemic) (150 mg, 35%).

Provenance & Evidence