1,5,6,7-Tetrahydro-4H-indol-4-one → 1-[4-(2,3-Dihydrobenzofuran-7-yl)-2-hydroxy-4-methyl-2-trifluoromethylpentyl]-1,5,6,7-tetrahydroindol-4-one

HRID 400691

반응식

HRID 400691 반응식
[CH3:1][C:2]([C:12]1[C:20]2[O:19][CH2:18][CH2:17][C:16]=2[CH:15]=[CH:14][CH:13]=1)([CH3:11])[CH2:3][C:4]1([C:7]([F:10])([F:9])[F:8])[CH2:6][O:5]1.[NH:21]1[C:29]2[CH2:28][CH2:27][CH2:26][C:25](=[O:30])[C:24]=2[CH:23]=[CH:22]1.[O-]CC.[Na+].C(=O)(O)[O-].[Na+]>C(O)C>[O:19]1[C:20]2[C:12]([C:2]([CH3:1])([CH3:11])[CH2:3][C:4]([OH:5])([C:7]([F:8])([F:10])[F:9])[CH2:6][N:21]3[C:29]4[CH2:28][CH2:27][CH2:26][C:25](=[O:30])[C:24]=4[CH:23]=[CH:22]3)=[CH:13][CH:14]=[CH:15][C:16]=2[CH2:17][CH2:18]1

참가 물질

6

반응물 4

HCID 2802291,5,6,7-Tetrahydro-4H-indol-4-oneHCID 516892Sodium BicarbonateHCID 2723922Sodium ethoxideHCID 577755187-[1,1-Dimethyl-2-(2-trifluoromethyloxiranyl)ethyl]-2,3-dihydrobenzofuran

생성물 1

HCID 600264231-[4-(2,3-Dihydrobenzofuran-7-yl)-2-hydroxy-4-methyl-2-trifluoromethylpentyl]-1,5,6,7-tetrahydroindol-4-one수율 66%

시약·촉매·용매 1

HCID 702Ethanol용매

반응 조건

온도
85 °C

실험 절차

To a suspension of 7-[1,1-dimethyl-2-(2-trifluoromethyloxiranyl)ethyl]-2,3-dihydrobenzofuran (59.2 mg, 0.21 mmol) and 1,5,6,7-tetrahydroindol-4-one (56.0 mg, 0.41 mmol) in 0.4 mL of anhydrous ethanol was added 0.077 mL of sodium ethoxide solution (21 wt % in ethanol). The reaction mixture was then heated at 85° C. for 16 hours. The resulting mixture was poured into half-saturated sodium bicarbonate and extracted with ethyl acetate. The combined organic phases were dried over sodium sulfate, filtered, and concentrated in vacuo. The residue was purified by silica gel chromatography (eluted with 35% ethyl acetate-hexanes) to give 58.4 mg (66% yield) of the title compound as a white solid, m.p. 145° C.-146° C.

후처리

  1. extractionextracted with ethyl acetate
  2. dry with materialThe combined organic phases were dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by silica gel chromatography (eluted with 35% ethyl acetate-hexanes)

출처 및 근거

ORD 기록
ord-b077ed2160254a968b0fff0f79d3f0f8
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08741897B2

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