Boron tribromide → HCID 178515923, compound

Participants

Reaction Steps

To a suspension of 2-[3-(4-methoxyphenyl)-1H-pyrazol-4-yl]benzothiazole (100 mg, 0.33 mmol) was slowly added tribromoborane (3.3 mL of a 1 M solution in CH2Cl2, 3.3 mmol). The mixture was stirred overnight. The reaction was then quenched by the addition of methanol. The mixture was neutralized with sodium carbonate solution and extracted three times with ethyl acetate. The organic extracts were combined, washed with brine, dried over Na2SO4, filtered, and evaporated. The crude material was recrystallized from ethyl acetate to yield 64 mg (66%) of the title compound as a yellow solid. MS (m/z, ES+): 294 (M+1, 100%). 1H NMR (400 MHz, ppm, DMSO-d6): δ 13.5 (br s, 1H), 9.80 (br s, 1H), 8.22 (br s, 1H), 7.98 (d, 3J=8.1 Hz, 1H), 7.91 (d, 3J=8.0 Hz, 1H), 7.47 (d, 3J=8.0 Hz, 2H), 7.45 (dd, 3J=7.4 Hz, 3J=8.1 Hz, 1H), 7.34 (dd, 3J=7.4 Hz, 3J=8.0 Hz, 1H), 6.89 (d, 3J=8.0 Hz, 2H).

Provenance & Evidence