Potassium Phosphate, Tribasic → HCID 118071161, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of Intermediate 156C (5 g, 12.7 mmol), (3-chloro-4-fluorophenyl)boronic acid (3.33 g, 19.12 mmol) in 1,4-dioxane (75 mL) and water (7.5 mL) was added and K3PO4 (8.12 g, 38.2 mmol) and the reaction mixture was purged with nitrogen for 5 min PdCl2(dppf)-CH2Cl2 (0.521 g, 0.637 mmol) was added and the reaction mixture was stirred at 80° C. for 12 h. The reaction mixture was diluted with water (75 mL) and extracted with EtOAc (3×75 mL). The combined organic layer was washed with brine, dried over Na2SO4, filtered and the filtrate concentrated. The crude reaction mixture was purified by silica gel chromatography (24 g REDISEP® column, eluting with 2% MeOH in CHCl3). Fractions were collected and concentrated to afford Intermediate 185A (4.2 g, 78%) as white solid. MS(ES): m/z=395 [M+H]+; 1H NMR 1H NMR (300 MHz, DMSO-d6) δ ppm 7.81-7.87 (m, 1H), 7.63-7.72 (m, 1H), 7.47 (s, 1H), 7.15-7.37 (m, 2H), 4.74 (s, 2H), 4.16 (s, 2H), 3.80-3.88 (m, 2H), 1.45 (s, 9H).

Provenance & Evidence