1,1-Dimethylethyl 2-(aminocarbonyl)-1-pyrrolidinecarboxylate → tert-Butyl 2-{[2-(1,1-dioxido-2,3-dihydro-1,4-benzothiazepin-4(5H)-yl)-6-methylquinolin-4-yl]carbamoyl}pyrrolidine-1-carboxylate

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-(4-chloro-6-methylquinolin-2-yl)-2,3,4,5-tetrahydro-1,4-benzothiazepine 1,1-dioxide (0.60 g, 1.6 mmol, prepared in analogy to the one in Example 2-1), tert-butyl 2-carbamoylpyrrolidine-1-carboxylate (0.34 g, 1.6 mmol), 1,1′-bis(diphenylphosphino)ferrocene-palladium(II)dichloride (0.13 g, 0.16 mmol), 1,1′-bis(diphenylphosphino)ferrocene (0.089 g, 0.16 mmol) and sodium tert-butoxide (0.307 g, 3.2 mmol) in 1,4-dioxane (25 mL) was heated with stirring for 1.5 hours at 120° C. under microwave irradiation. The reaction mixture was filtered and concentrated in vacuo. The residue was purified by preparative TLC (eluting with 50% ethyl acetate in petroleum ether, V/V=1:1) to give 250 mg of the desired product (yield was 29%).

Provenance & Evidence