1-Methyl-3-(trifluoroacetyl)-1H-indole → HCID 59437212, 화합물

HRID 244465

반응식

HRID 244465 반응식
Br[C:2]1[CH:19]=[CH:18][C:5]2[N:6]([C:11]3[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=3)[C:7](=[O:10])[N:8]([CH3:9])[C:4]=2[CH:3]=1.C([Li])(C)(C)C.[F:25][C:26]([F:40])([F:39])[C:27]([C:29]1[C:37]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[N:31]([CH3:38])[CH:30]=1)=[O:28]>C1COCC1>[F:17][C:14]1[CH:15]=[CH:16][C:11]([N:6]2[C:5]3[CH:18]=[CH:19][C:2]([C:27]([OH:28])([C:29]4[C:37]5[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=5)[N:31]([CH3:38])[CH:30]=4)[C:26]([F:25])([F:40])[F:39])=[CH:3][C:4]=3[N:8]([CH3:9])[C:7]2=[O:10])=[CH:12][CH:13]=1

참가 물질

5

반응물 3

HCID 35243881-Methyl-3-(trifluoroacetyl)-1H-indoleHCID 594372865-Bromo-1-(4-fluorophenyl)-3-methyl-1,3-dihydro-benzimidazol-2-oneHCID 178418306HCID 178418306, 화합물

생성물 1

HCID 59437212HCID 59437212, 화합물수율 12.8%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

To a chilled (−78° C.) solution of 5-bromo-1-(4-fluorophenyl)-3-methyl-1,3-dihydro-benzimidazol-2-one (80 mg, 0.25 mmol) in anhydrous THF (3 mL) was added tert-butyllithium (0.2 mL of 1.7 M solution in heptane, 0.34 mmol). After 1 minute, a chilled (−78° C.) solution of 2,2,2-trifluoro-1-(1-methyl-1H-indol-3-yl)ethanone (57 mg, 0.25 mmol) in anhydrous THF (1 mL) was added. After 10 minutes, the mixture was quenched with ammonium chloride solution and extracted with three 15 mL portions of methylene chloride. The combined organic layers were washed with water, dried over anhydrous sodium sulfate, and concentrated in vacuo to afford a brownish oil. The residue was purified by column chromatography over silica gel eluting with 0-10% ethyl acetate in methylene chloride to afford 15 mg of the title compound as a white powder. MS m/z 470 (MH+).

후처리

  1. additionwas added
  2. waitAfter 10 minutes
  3. customthe mixture was quenched with ammonium chloride solution
  4. extractionextracted with three 15 mL portions of methylene chloride
  5. washThe combined organic layers were washed with water
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated in vacuo
  8. customto afford a brownish oil
  9. customThe residue was purified by column chromatography over silica gel eluting with 0-10% ethyl acetate in methylene chloride

출처 및 근거

ORD 기록
ord-b80428248671469ab8751842b05dafcb
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08658637B2

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