Diisopropylamine → HCID 59252689, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-bromo-4-fluoroaniline (5.0 g, 26.3 mmol) in DMF/water (80/20 v/v, 65.8 ml) under an atmosphere of nitrogen were added 4-(methanesulfonyl)phenylboronic acid (7.9 g, 39.5 mmol), tris(4,6-dimethyl-3-sulfanatophenyl)phosphine trisodium salt hydrate (2.6 g, 4.0 mmol), palladium(II) acetate (0.3 g, 1.3 mmol), and diisopropyl amine (11.3 ml, 79.0 mmol). The reaction was allowed to stir at 50° C. for 2.5 h. The reaction was diluted with EtOAc and washed with 3M LiCl (3×), water, and brine. The organic portion was dried over sodium sulfate, filtered, and concentrated in vacuo to afford 4-fluoro-4′-(methylsulfonyl)-1,1′-biphenyl-2-amine as a yellow solid (95%). LCMS (M+H) 266.1. 1H NMR (400 MHz, CD3OD) δ 8.02 (m, 2H), 7.65 (m, 2H), 7.05 (dd, J=8.6, 6.2 Hz, 1H), 6.57-6.47 (m, 2H), 3.86 (s, 2H), 3.11 (s, 3H).

Provenance & Evidence