Trifluoroacetic acid → 3-(6-hydroxy-1,3-benzodioxol-5-yl)-7-(trifluoromethyl)-1,3-dihydro-2H-indol-2-one

HRID 2385045노트

반응식

HRID 2385045 반응식
O[C:2]1([C:16]2[C:24]([OH:25])=[CH:23][C:19]3[O:20][CH2:21][O:22][C:18]=3[CH:17]=2)[C:10]2[C:5](=[C:6]([C:11]([F:14])([F:13])[F:12])[CH:7]=[CH:8][CH:9]=2)[NH:4][C:3]1=[O:15].FC(F)(F)C(O)=O.C([SiH](CC)CC)C>>[OH:25][C:24]1[C:16]([CH:2]2[C:10]3[C:5](=[C:6]([C:11]([F:14])([F:13])[F:12])[CH:7]=[CH:8][CH:9]=3)[NH:4][C:3]2=[O:15])=[CH:17][C:18]2[O:22][CH2:21][O:20][C:19]=2[CH:23]=1

참가 물질

4

반응물 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 673566523-hydroxy-3-(6-hydroxy-1,3-benzodioxol-5-yl)-7-(trifluoromethyl)-1,3-dihydro-2H-indol-2-one

생성물 1

HCID 673588353-(6-hydroxy-1,3-benzodioxol-5-yl)-7-(trifluoromethyl)-1,3-dihydro-2H-indol-2-one수율 88.1%

실험 절차

To a solution of 3-hydroxy-3-(6-hydroxy-1,3-benzodioxol-5-yl)-7-(trifluoromethyl)-1,3-dihydro-2H-indol-2-one (7.06 g, 20.0 mmol) in anhydrous trifluoroacetic acid (21.0 mL, 9.12 g, 80 mmol) was added triethylsilane (12.8 mL, 9.30 g, 80.0 mmol) at ambient temperature. The reaction mixture was stirred at ambient temperature for 0.5 h. The reaction mixture was quenched with water (50.0 mL). The mixture was extracted with ethyl acetate (2×150 mL). The organic solution was washed with saturated ammonium chloride (3×75 mL), dried over sodium sulfate and filtered. The filtrate was concentrated in vacuo to dryness. The residue was triturated with diethyl ether to afford 3-(6-hydroxy-1,3-benzodioxol-5-yl)-7-(trifluoromethyl)-1,3-dihydro-2H-indol-2-one (5.94 g, 88%) as colourless solid: 1H NMR (300 MHz, DMSO-d6) δ 10.81 (s, 1H), 9.25 (br, 1H), 7.37 (d, J=8.0 Hz, 1H), 7.12 (d, J=7.3 Hz, 1H), 6.98 (dd, J=7.7, 7.7 Hz, 1H), 6.71 (s, 1H), 5.88 (s, 2H), 4.65 (s, 1H); 13C NMR (75 MHz, DMSO-d6) δ 178.7, 150.5, 147.4, 140.5, 140.1, 133.3, 127.8, 124.3, 124.2, 121.6, 115.5, 110.8, 110.3, 101.3, 98.2, 48.1; MS (ES+) m/z 338.3 (M+1).

후처리

  1. customThe reaction mixture was quenched with water (50.0 mL)
  2. extractionThe mixture was extracted with ethyl acetate (2×150 mL)
  3. washThe organic solution was washed with saturated ammonium chloride (3×75 mL)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated in vacuo to dryness
  7. customThe residue was triturated with diethyl ether

출처 및 근거

ORD 기록
ord-693283b095b544399df66f364b9956bf
출처 데이터셋
uspto-grants-2012_09
특허 번호
US08263606B2

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