Sodium Carbonate → HCID 86704620, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of the title compound from Step B (400 mg, 0.596 mmol), methyl 3-methyl-4-(4,4,5,5-tetramethyl-1-3,2-dioxaborolan-2-yl)benzoate (247 mg, 0.894 mmol), Na2CO3 (139 mg, 1.31 mmol) and catalytic amount of Pd(PPh3)4 was mixed in water/EtOH/toluene (1:2:4) (7 mL). The mixture was stirred at 80° C. for 1 h. The mixture was cooled, and the solvents were removed. Water (5 mL) was added and the mixture was extracted with dichloromethane (3×5 mL). The combined organic fractions were washed with brine (5 mL), dried (Na2SO4), filtered and the solvent was evaporated under reduced pressure. The residue was purified by column chromatography on silica gel Biotage 40S, eluting with EtOAc/hexane (2:8) to give the title compound as a yellow gum. 1H NMR (CDCl3, 500 MHz) δ 8.47 (s, 1H), 8.02 (s, 1H), 7.96 (d, J=8 Hz, 1H), 7.92 (s, 1H), 7.78 (s, 2H), 7.33 (m, 4H), 5.76 (d, J=8.0 Hz, 1H), 4.98 (d, J=17 Hz, 1H), 4.46 (m, 1H), 4.13 (d, J=17 Hz, 1H), 3.97 (s, 3H), 2.65 (s, 3H), 2.33 (s, 3H), 0.78 (d, J=6.5 Hz, 3H).

Provenance & Evidence