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Benzoyl chloride → Phenyl-{5-[2,2,2-trifluoro-1-hydroxy-1-(1-methyl-1H-indol-3-yl)ethyl]indazol-1-yl}methanone

HRID 244416
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HRID 244416 반응식
[F:1][C:2]([F:25])([F:24])[C:3]([C:15]1[CH:16]=[C:17]2[C:21](=[CH:22][CH:23]=1)[NH:20][N:19]=[CH:18]2)([C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[N:7]([CH3:14])[CH:6]=1)[OH:4].[C:26](Cl)(=[O:33])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>N1C=CC=CC=1.CCOCC.O>[C:27]1([C:26]([N:20]2[C:21]3[C:17](=[CH:16][C:15]([C:3]([OH:4])([C:5]4[C:13]5[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=5)[N:7]([CH3:14])[CH:6]=4)[C:2]([F:1])([F:24])[F:25])=[CH:23][CH:22]=3)[CH:18]=[N:19]2)=[O:33])[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1
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6

반응물 2

HCID 7412Benzoyl chlorideHCID 594372242,2,2-trifluoro-1-(1H-indazol-5-yl)-1-(1-methyl-1H-indol-3-yl)ethanol

생성물 1

HCID 59437295Phenyl-{5-[2,2,2-trifluoro-1-hydroxy-1-(1-methyl-1H-indol-3-yl)ethyl]indazol-1-yl}methanone수율 57.4%

시약·촉매·용매 3

HCID 962Water용매HCID 1049Pyridine용매
HCID 3283
Diethyl Ether
용매

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온도
100 °C

실험 절차

A mixture of 2,2,2-trifluoro-1-(1H-indazol-5-yl)-1-(1-methyl-1H-indol-3-yl)ethanol (0.162 mmol) and benzoyl chloride (0.324 mmol) in 1 mL pyridine was heated at 100° C. After 2 hours, the mixture was cooled to room temperature and diluted with ether and water. The organic layer was washed with aqueous HCl and brine and dried over magnesium sulfate. The volatiles were removed in vacuo and the residue purified by flash silica gel chromatography using 33% ethyl acetate in hexanes. The product-rich fractions were concentrated in vacuo to provide 0.093 mmol of the title compound, m.p. 102° C.-103° C.

후처리

  1. temperaturethe mixture was cooled to room temperature
  2. washThe organic layer was washed with aqueous HCl and brine
  3. dry with materialdried over magnesium sulfate
  4. customThe volatiles were removed in vacuo
  5. customthe residue purified by flash silica gel chromatography
  6. concentrationThe product-rich fractions were concentrated in vacuo

출처 및 근거

ORD 기록
ord-9b342229bb9b4af99ec8604f724d6e34
출처 데이터셋
uspto-grants-2014_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08658637B2

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