Triethylamine → HCID 71571671, compound

Participants

Reaction Steps

The mixture of (E)-1-hydroxy-3,3-dimethyl-1,3-dihydrobenzo[c][1,2]oxaborole-5-carbaldehyde oxime (62 mg, 0.3 mmol) and NCS (48 mg, 0.36 mmol) in DMF (2 mL) was stirred at rt overnight. To the mixture was added 1,3-dichloro-2-methyl-5-(3,3,3-trifluoroprop-1-en-2-yl)benzene (75 mg, 0.3 mmol) and Et3N (0.1 mL) and the mixture was stirred at rt for 4 h. It was partitioned between EA and H2O. The organic layer was washed with H2O, brine, dried over Na2SO4, concentrated under vacuum. The residue was purified to give the desired product (30 mg, 21.8% yield). 1H NMR (400 MHz, DMSO-d6): δ 9.20 (s, 1H), 7.77-7.70 (m, 3H), 7.63 (s, 2H), 4.42 (d, J=18.4 Hz, 1H), 4.30 (d, J=18.4 Hz, 1H), 2.45 (s, 3H), 1.48 (d, J=2.4 Hz, 6H), ppm; HPLC purity: 98.6% at 220 nm and 98.9% at 254 nm; MS: m/z=458.5 (M+1, ESI+).

Provenance & Evidence