1,1'-Carbonyldiimidazole → 5-[1-(1-Methyl-1H-indol-3-yl)-2,2,2-trifluoro-1-hydroxyethyl]indazole-1-carboxylic acid cyclobutyl ester

HRID 244420노트

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HRID 244420 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](N1C=CN=C1)(N1C=CN=C1)=[O:27].[CH:38]1([OH:42])[CH2:41][CH2:40][CH2:39]1>N1C=CC=CC=1>[CH:38]1([O:42][C:26]([N:20]2[C:21]3[C:17](=[CH:16][C:15]([C:3]([C:5]4[C:13]5[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=5)[N:7]([CH3:14])[CH:6]=4)([OH:4])[C:2]([F:1])([F:24])[F:25])=[CH:23][CH:22]=3)[CH:18]=[N:19]2)=[O:27])[CH2:41][CH2:40][CH2:39]1

참가 물질

5

반응물 3

HCID 682631,1'-CarbonyldiimidazoleHCID 76218CyclobutanolHCID 594372242,2,2-trifluoro-1-(1H-indazol-5-yl)-1-(1-methyl-1H-indol-3-yl)ethanol

생성물 1

HCID 594372515-[1-(1-Methyl-1H-indol-3-yl)-2,2,2-trifluoro-1-hydroxyethyl]indazole-1-carboxylic acid cyclobutyl ester수율 53.5%

시약·촉매·용매 1

HCID 1049Pyridine용매

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온도
80 °C

실험 절차

A mixture of 2,2,2-trifluoro-1-(1H-indazol-5-yl)-1-(1-methyl-1H-indol-3-yl)ethanol (0.142 mmol) and carbonyldiimidazole (0.185 mmol) in 1 mL of pyridine was heated at 80° C. for 10 hours, cooled to room temperature, and cyclobutanol (1.4 mmol) was added. The mixture was stirred overnight. The volatiles were removed 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 0.076 mmol of the desired compound, m.p. 82° C.-84° C.

후처리

  1. temperaturecooled to room temperature
  2. customThe volatiles were removed
  3. customthe residue purified by flash silica gel chromatography
  4. concentrationThe product-rich fractions were concentrated in vacuo

출처 및 근거

ORD 기록
ord-54aebfaef37247b9a8c92cfd356e3117
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08658637B2

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