反应详情

HATU (350 mg, 0.92 mmol) was added to CH3CN (5 mL) at 0° C. After stirring for 5 min, the mixture was added to a solution of 4-(5-(3,5-dichloro-4-fluorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-2-methylbenzoic acid (200 mg, 0.46 mmol), 5-(aminomethyl)-3,3-dimethylbenzo[c][1,2]oxaborol-1(3H)-ol hydrochloride (157 mg, 0.69 mmol), and TEA (186 mg, 1.83 mmol) in CH3CN (8 mL). Then the solution was stirred at rt for 2 h. The solution was acidified with HCl (1 N) and extracted with EA. The combined organic layers were washed with brine, dried over Na2SO4, and concentrated under reduced pressure. The residue was purified by prep-TLC (PE:EA=2:1) to give the final title compound (150 mg, yield 54%). 1H NMR (300 MHz, DMSO-d6): δ 8.98 (s, 1H), 8.92 (t, J=6.0 Hz, 1H), 7.78 (d, 2H), 7.62-7.58 (m, 3H), 7.48-7.45 (m, 1H), 7.33-7.27 (m, 2H), 4.49 (d, 2H), 4.39-4.25 (m, 2H), 2.36 (s, 3H), 1.42 (s, 6H); HPLC purity: 97.6% at 254 nm; MS: m/z=609 [M+H]+.

1. stirringThen the solution was stirred at rt for 2 h
2. extractionextracted with EA
3. washThe combined organic layers were washed with brine
4. dry with materialdried over Na2SO4
5. concentrationconcentrated under reduced pressure
6. customThe residue was purified by prep-TLC (PE:EA=2:1)