Tetrahydrofuran → HCID 66832128、化合物

HRID 58773ノート

反応式

HRID 58773 の反応式
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[Cl:19][C:20]1[CH:21]=[C:22]2[C:28]([CH2:29][CH2:30][NH:31][C:32]([C:34]3[CH:38]=[C:37]([CH2:39][C:40]4[CH:45]=[C:44]([F:46])[CH:43]=[CH:42][C:41]=4[F:47])[O:36][N:35]=3)=[O:33])=[C:27]([Si](CC)(CC)CC)[NH:26][C:23]2=[N:24][CH:25]=1.C1C[O:58]CC1>>[Cl:19][C:20]1[CH:21]=[C:22]2[C:28]([CH2:29][CH2:30][NH:31][C:32]([C:34]3[CH:38]=[C:37]([C:39](=[O:58])[C:40]4[CH:45]=[C:44]([F:46])[CH:43]=[CH:42][C:41]=4[F:47])[O:36][N:35]=3)=[O:33])=[CH:27][NH:26][C:23]2=[N:24][CH:25]=1

参加物

4

反応物 3

HCID 8028Tetrahydrofuran2 回HCID 2724141Tetrabutylammonium FluorideHCID 66832015N-(2-(5-chloro-2-(triethylsilyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)ethyl)-5-(2,5-difluorobenzyl)isoxazole-3-carboxamide

生成物 1

HCID 66832128HCID 66832128、化合物収率 22%

実験手順

A solution of tetrabutylammonium fluoride 1M in THF (1 mL; 1 mmol) was added to a solution of N-(2-(5-chloro-2-(triethylsilyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)ethyl)-5-(2,5-difluorobenzyl)isoxazole-3-carboxamide (0.105 g, 0.198 mmol) in THF (5 mL). The mixture was stirred overnight at room temperature and was evaporated. The residue was dissolved in dichloromethane, and the organic solution was washed with water and was concentrated under reduced pressure. The crude material was purified twice by flash chromatography on silica gel (eluent: 0 to 40% of ethyl acetate in dichloromethane) to give 0.019 g (22%) of N-(2-(5-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)ethyl)-5-(2,5-difluorobenzoyl)isoxazole-3-carboxamide as a white solid.

後処理

  1. customwas evaporated
  2. dissolutionThe residue was dissolved in dichloromethane
  3. washthe organic solution was washed with water
  4. concentrationwas concentrated under reduced pressure
  5. customThe crude material was purified twice by flash chromatography on silica gel (eluent: 0 to 40% of ethyl acetate in dichloromethane)

出典と根拠

ORDレコード
ord-5cc08393b6654dfd95d5f247c4584ce9
出典データセット
uspto-grants-2016_09
特許番号
US09434722B2

反応ノート

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