4-Azaindole → 4-(5-Chloro-2,3-dihydrobenzofuran-7-yl)-1,1,1-trifluoro-4-methyl-2-pyrrolo [3,2-b]pyridin-1-ylmethylpentan-2-ol

HRID 400690ノート

反応式

HRID 400690 の反応式
[NH:1]1[C:9]2[C:4](=[N:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[H-].[Na+].[Cl:12][C:13]1[CH:14]=[C:15]([C:22]([CH3:32])([CH3:31])[CH2:23][C:24]2([C:27]([F:30])([F:29])[F:28])[CH2:26][O:25]2)[C:16]2[O:20][CH2:19][CH2:18][C:17]=2[CH:21]=1>CN(C=O)C.C(OCC)(=O)C>[Cl:12][C:13]1[CH:14]=[C:15]([C:22]([CH3:32])([CH3:31])[CH2:23][C:24]([CH2:26][N:1]2[C:9]3[C:4](=[N:5][CH:6]=[CH:7][CH:8]=3)[CH:3]=[CH:2]2)([OH:25])[C:27]([F:28])([F:29])[F:30])[C:16]2[O:20][CH2:19][CH2:18][C:17]=2[CH:21]=1

参加物

6

反応物 3

HCID 92264-AzaindoleHCID 24758Sodium hydrideHCID 600263575-Chloro-7-[1,1-dimethyl-2-(2-trifluoromethyloxiranyl)ethyl]-2,3-dihydrobenzofuran

生成物 1

HCID 114192624-(5-Chloro-2,3-dihydrobenzofuran-7-yl)-1,1,1-trifluoro-4-methyl-2-pyrrolo [3,2-b]pyridin-1-ylmethylpentan-2-ol収率 45%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

A solution of 1H-pyrrolo[3,2-b]pyridine (33.0 mg, 0.279 mmol) in 4 mL of DMF was treated with NaH (60% in mineral oil, 16.8 mg, 0.419 mmol) at room temperature. After 30 minutes, 5-chloro-7-[1,1-dimethyl-2-(2-trifluoromethyloxiranyl)ethyl]-2,3-dihydrobenzofuran (188 mg, 0.558 mmol) was added and the resulting mixture was stirred overnight. The reaction was then diluted with 5 mL of ethyl acetate and quenched with 5 mL of saturated ammonium chloride solution. The aqueous layer was extracted with 5 mL of ethyl acetate. The combined organic layers were dried over magnesium sulfate, filtered, and concentrated in vacuo. The residue was triturated with diethyl ether to afford 55.0 mg (45% yield) of the title product as white solid.

後処理

  1. customquenched with 5 mL of saturated ammonium chloride solution
  2. extractionThe aqueous layer was extracted with 5 mL of ethyl acetate
  3. dry with materialThe combined organic layers were dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was triturated with diethyl ether

出典と根拠

ORDレコード
ord-07b93d38d29d433087c39ef056b6d833
出典データセット
uspto-grants-2014_06
特許番号
US08741897B2

反応ノート

読み込み中…