Potassium Phosphate, Tribasic → HCID 118071191, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred suspension of Intermediate 350F (0.400 g, 0.956 mmol) in 1,4-dioxane (5 mL) was added K3PO4 (0.500 g, 2.80 mmol), (3-chloro-4-fluorophenyl) boronic acid (0.250 g, 1.435 mmol) and the reaction mixture was purged with nitrogen for 10 min. PdCl2(dppf)-CH2Cl2 (0.047 g, 0.057 mmol) was then added and the reaction mixture was heated to 80° C. and stirred for 12 h. The reaction mixture was diluted with water (25 mL) and extracted with EtOAc (3×25 mL) The combined organic layers were washed with brine, dried over Na2SO4, filtered and the filtrate concentrated. The crude product was purified by silica gel chromatography (24 g REDISEP® column, eluting with 3% MeOH in CHCl3). Fractions containing the product were combined and evaporated to afford Intermediate 350G as a pale yellow solid (0.29 g, 70%). MS(ES): m/z=421 [M+H]+; 1H NMR (400 MHz, chloroform-d) δ ppm 7.69 (dd, J=7.0, 2.3 Hz, 1H), 7.50 (ddd, J=8.5, 4.6, 2.1 Hz, 1H), 7.33-7.15 (m, 1H), 5.34 (br. s., 2H), 4.97 (br. s., 2H), 4.05 (br. s., 2H), 1.44 (s, 9H), 1.22-1.24 (m, 2H), 1.02-0.79 (m, 2H).

Provenance & Evidence