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Isopropyl chloroformate → 5-[1-(1-Methyl-1H-indol-3-yl)-2,2,2-trifluoro-1-hydroxyethyl]indazole-1-carboxylic acid isopropyl ester

HRID 244419
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인쇄 미리보기

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HRID 244419 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].Cl[C:27]([O:29][CH:30]([CH3:32])[CH3:31])=[O:28]>C1(C)C=CC=CC=1.N1C=CC=CC=1.CCOCC.O>[CH:30]([O:29][C:27]([N:20]1[C:21]2[C:17](=[CH:16][C:15]([C:3]([C:5]3[C:13]4[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=4)[N:7]([CH3:14])[CH:6]=3)([OH:4])[C:2]([F:1])([F:24])[F:25])=[CH:23][CH:22]=2)[CH:18]=[N:19]1)=[O:28])([CH3:32])[CH3:31]
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7

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HCID 7917Isopropyl chloroformateHCID 594372242,2,2-trifluoro-1-(1H-indazol-5-yl)-1-(1-methyl-1H-indol-3-yl)ethanol

생성물 1

HCID 594372315-[1-(1-Methyl-1H-indol-3-yl)-2,2,2-trifluoro-1-hydroxyethyl]indazole-1-carboxylic acid isopropyl ester

시약·촉매·용매 4

HCID 962Water용매HCID 1049Pyridine용매
HCID 1140
Toluene
용매
HCID 3283Diethyl Ether용매

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온도
85 °C

실험 절차

A mixture of 2,2,2-trifluoro-1-(1H-indazol-5-yl)-1-(1-methyl-1H-indol-3-yl)ethanol (0.165 mmol) and isopropyl chloroformate (0.49 mmol from a 1.0 M solution in toluene) in 1 mL of pyridine was heated at 85° C. for 10 hours, cooled to room temperature, and diluted with ether and water. The organic layer was washed with water and brine and dried over magnesium sulfate. The volatiles were concentrated 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 afford 0.069 mmol of the desired compound, m.p. 105° C.-106° C.

후처리

  1. temperaturecooled to room temperature
  2. washThe organic layer was washed with water and brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationThe volatiles were concentrated 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-4f6c81ff658b4ff0aca55d9b1ba68360
출처 데이터셋
uspto-grants-2014_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08658637B2

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