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

HRID 244420ノート

反応式

HRID 244420 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

反応条件

温度
80 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-54aebfaef37247b9a8c92cfd356e3117
出典データセット
uspto-grants-2014_02
特許番号
US08658637B2

反応ノート

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