4-Fluorobenzylamine → 7-Bromo-2-cyclopropyl-N-[(4-fluorophenyl)-methyl]-4-methyl-quinoline-3-carboxylic acid amide

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 1.0 g (2.99 mmol) 7-bromo-2-cyclopropyl-4-methylquinoline-3-carboxylic acid ethyl ester in toluene (10 ml) were added 10.5 ml (2M solution in toluene, 20.9 mmol) Me3Al at RT followed by the addition of 3.74 g (29.9 mmol) 4-fluorobenzylamine. The reaction mixture was heated at 120° C. for 16 h. Then the reaction was quenched with water (15 ml) and extracted with EtOAc (3×30 ml). The combined organic layers were washed with 2N aq. HCl and brine, dried over MgSO4 and concentrated in vacuum. After CC (EtOAc/cyclohexane 1:2) of the residue, 900 mg (2.2 mmol, 73%) 7-Bromo-2-cyclopropyl-N-[(4-fluorophenyl)-methyl]-4-methyl-quinoline-3-carboxylic acid amide (example 28) were obtained. MS: m/z 413.1 [M+H]+.

Provenance & Evidence