3-Bromo-o-toluidine → HCID 59375104, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 3-bromo-2-methylaniline (200 mg, 1.075 mmol), 2-fluoro-4-methylpyridine (155 mg, 1.397 mmol) and potassium tert-butoxide (193 mg, 1.72 mmol) in DMSO (4 mL) was heated in a sealed tube via microwave irradiation at 190° C. for 40 min. The mixture was partitioned between EtOAc and water, and the organic phase was washed with brine, dried and concentrated. The residue was purified by column chromatography (eluting with a gradient from hexane to 85:15 hexane-EtOAc) to provide N-(3-bromo-2-methylphenyl)-4-methylpyridin-2-amine as a yellow solid (100 mg, 34%). 1H NMR (400 MHz, chloroform-d) δ 8.05 (1H, d, J=5.3 Hz), 7.38 (2H, d, J=8.1 Hz), 7.06 (1H, t, J=8.0 Hz), 6.58 (1H, d, J=5.3 Hz), 6.40 (1H, s), 6.23 (1H, br. s.), 2.37 (3H, s), 2.23 (3H, s). Mass spectrum m/z 277, 279 (M+H)+.

Provenance & Evidence