반응 #1107994

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5,6-dichloro-2-(4-oxopentyloxy)nicotinonitrile

benzo[c][1,2]oxaborole-1,5(3H)-diol

Cs2CO3

→

5-Chloro-6-(1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-5-yloxy)-2-(4-oxopentyloxy)nicotinonitrile

용매

DMSO

반응 조건

후처리

1. 1
   기타Into a 250-mL 3-necked round-bottom flask purged
2. 2
   온도maintained with an inert atmosphere of nitrogen
3. 3
   기타quenched by the addition of 100 mL of ice water
4. 4
   추출The resulting solution was extracted with 3×50 mL of ethyl acetate
5. 5
   세척washed with 2×50 mL of water and 1×50 mL of brine
6. 6
   건조dried over Na2SO4
7. 7
   농축concentrated under vacuum
8. 8
   기타This resulted in 1.3 g (80%) of 5-chloro-6-(1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-5-yloxy)-2-(4-oxopentyloxy)nicotinonitrile as a white solid

실험 절차

Into a 250-mL 3-necked round-bottom flask purged and maintained with an inert atmosphere of nitrogen were placed a solution of 5,6-dichloro-2-(4-oxopentyloxy)nicotinonitrile (1.12 g, 4.12 mmol, 1.00 equiv) in DMSO (50 mL), benzo[c][1,2]oxaborole-1,5(3H)-diol (650 mg, 4.33 mmol, 1.05 equiv) and Cs2CO3 (1.60 g, 4.92 mmol, 1.20 equiv). The resulting solution was stirred for 2 h at 40° C., then quenched by the addition of 100 mL of ice water. The resulting solution was extracted with 3×50 mL of ethyl acetate. The organic layers were combined, washed with 2×50 mL of water and 1×50 mL of brine, then dried over Na2SO4 and concentrated under vacuum. This resulted in 1.3 g (80%) of 5-chloro-6-(1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-5-yloxy)-2-(4-oxopentyloxy)nicotinonitrile as a white solid. LC-MS (ES, m/z): 387 [M+H]+. 1H-NMR (300 MHz, DMSO-d6) δ (ppm) 9.28 (1H, s), 8.60 (1H, s), 7.81 (1H, d, J=7.8 Hz), 7.33 (1H, s), 7.25 (1H, d, J=7.8 Hz), 5.02 (2H, s), 4.00 (2H, t), 2.35 (2H, t), 2.05 (3H, s), 1.8-1.6 (2H, m).

출처