Sodium Carbonate → HCID 71571902, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-(3-chloro-4,5-difluorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1.2 g, 4.38 mmol), 2-bromo-3,3,3-trifluoroprop-1-ene (920 mg, 5.26 mmol, 1.2 eq), Na2CO3 (1.39 g, 13.14 mmol, 3 eq) and Pd(dppf)Cl2 (358 mg, 10% mol) in DME (50 mL) and water (2 mL) was heated at 70 to 80° C. for 2 h. The mixture was cooled to 0° C. with ice-water bath, and then used to next step without work-up. To the reaction mixture were added TEA (1.33 g, 1.83 mL, 13.14 mmol, 3 eq) and N,1-dihydroxy-3,3-dimethyl-1,3-dihydrobenzo[c][1,2]oxaborole-5-carbimidoyl chloride (841 mg, 3.50 mmol, 0.8 eq) at 0° C. The reaction mixture was stirred for 12 h at rt, poured into ice-water and extracted with EA. The organic layer was washed with brine, dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by silica gel column and prep-HPLC to give 125 mg final title product. 1H NMR (400 MHz, DMSO-d6): δ 9.22 (s, 1 H), 7.76-7.66 (m, 5 H), 4.43 (d, J=18.4 Hz, 1 H), 4.31 (d, J=18.4 Hz, 1 H), 1.48 (s,6 H) ppm; MS: m/z=444/504 (M−1, ESI−).

Provenance & Evidence