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

反応式

HRID 400691 の反応式
[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

参加物

6

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

反応条件

温度
85 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-b077ed2160254a968b0fff0f79d3f0f8
出典データセット
uspto-grants-2014_06
特許番号
US08741897B2

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