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

HRID 1965318ノート

反応式

HRID 1965318 の反応式
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

参加物

4

反応物 3

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

生成物 1

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

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-08b569b7ef61445b945ec480db5df52f
出典データセット
uspto-grants-2013_04
特許番号
US08415370B2

反応ノート

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