Triethylamine → HCID 68238986, compound

Participants

Reaction Steps

A solution of 3,3-dimethyl-7-nitro-3,4-dihydro-benzo[c][1,2]oxaborinin-1-ol (80 mg, 0.36 mmol) in dry THF (8 mL) was passed through a Thales Nano H-Cube hydrogenator (10% Pd/C catalyst, 1 mL/min flow rate, 1 atm, 30° C.), flushing with an additional 2 mL of THF. To the reaction solution was then added an excess of triethylamine (0.3 mL) and 4-fluoro-2-trifluoromethylbenzoyl chloride (100 mg, 0.44 mmol). The reaction was stirred at room temperature for 16 hours, and then diluted with aqueous hydrochloric acid (10 mL, 1 M). After vigorous mixing, the mixture was extracted with EtOAc (3×5 mL). The combined organic portions were dried over magnesium sulfate and concentrated to dryness. The crude product was purified by silica gel chromatography to produce the title compound as a white solid. LCMS (M/Z): 382 (M+H); 1H NMR (400 MHz, DMSO-d6) δ ppm 1.25 (s, 6H) 2.83 (s, 2H) 7.14 (d, J=8.4 Hz, 1H) 7.55-7.73 (m, 2H) 7.71-7.86 (m, 2H) 7.90 (d, J=2.3 Hz, 1H) 8.35 (s, 1H) 10.47 (s, 1H).

Provenance & Evidence