3-Fluoro-4-methoxyaniline → HCID 59781130, compound

Participants

Reaction Conditions

Reaction Steps

5-bromo-2-chloro-N-phenylnicotinamide (224 mg, 719 μmol) and 3-fluoro-4-methoxybenzenamine (316.7 mg, 2244 μmol) were suspended in isoamyl alcohol (1.5 ml) in a reaction microwave vessel which was sealed. This vessel was heated in the Biotage Initiator microwave at 200° C. for 20 minutes, with 45 seconds of stirring beforehand, and then cooled to room temperature. This process was repeated using 5-bromo-2-chloro-N-phenylnicotinamide (810 mg, 2.60 mmol) and 3-fluoro-4-methoxybenzenamine (1.092 g, 7.74 mmol), and isoamyl alcohol (7.5 ml), and then repeated a third time with 5-bromo-2-chloro-N-phenylnicotinamide (1.643 g, 5.28 mmol), 3-fluoro-4-methoxybenzenamine (2.285 g, 16 mmol), and isoamyl alcohol (10 ml). These three sets of reaction were combined, concentrated, treated with Et2O, and filtered. The solid was washed with Et2O, and the filtrate was concentrated and purified on a silica gel filter (˜3 inches, DCM) to afford the desired 5-bromo-2-(3-fluoro-4-methoxyphenylamino)-N-phenylnicotinamide (3.49 g, 8.39 mmol, 75% yield). MS (ESI pos. ion) m/z: 416 (MH+, 79Br), 418 (MH+, 81Br). Calc'd exact mass for C19H15BrFN3O2: 415 (79Br), 417 (81Br).

Provenance & Evidence