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Methyl iodide → 4-{3-[2,6-bis(trifluoromethyl)pyridin-4-yl]-3-(trifluoromethyl)-3,4-dihydro-2H-pyrrol-5-yl}-2-bromobenzyl acetate

HRID 2172532
ノート
印刷プレビュー

反応式

HRID 2172532 の反応式
CC([O-])(C)C.[K+].[C:7]([O:10][CH2:11][C:12]1[CH:17]=[CH:16][C:15]([C:18](=S)[NH:19][CH2:20][Si](C)(C)C)=[CH:14][C:13]=1[Br:26])(=[O:9])[CH3:8].IC.[F:29][C:30]([F:48])([F:47])[C:31]1[CH:36]=[C:35]([C:37]([C:39]([F:42])([F:41])[F:40])=[CH2:38])[CH:34]=[C:33]([C:43]([F:46])([F:45])[F:44])[N:32]=1.[N+](CCCC)(CCCC)(CCCC)CCCC.[F-]>C1COCC1.C(OC)(C)(C)C>[C:7]([O:10][CH2:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[CH2:38][C:37]([C:35]3[CH:36]=[C:31]([C:30]([F:29])([F:47])[F:48])[N:32]=[C:33]([C:43]([F:46])([F:44])[F:45])[CH:34]=3)([C:39]([F:42])([F:41])[F:40])[CH2:20][N:19]=2)=[CH:14][C:13]=1[Br:26])(=[O:9])[CH3:8]
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 5

HCID 6328Methyl iodideHCID 2724141Tetrabutylammonium FluorideHCID 23665647Potassium tert-butoxideHCID 580920912-Bromo-4-{[(trimethylsilyl)methyl]carbamothioyl}benzyl acetateHCID 866646212,6-Bis(trifluoromethyl)-4-(3,3,3-trifluoroprop-1-en-2-yl)pyridine

生成物 1

HCID 86664622
4-{3-[2,6-bis(trifluoromethyl)pyridin-4-yl]-3-(trifluoromethyl)-3,4-dihydro-2H-pyrrol-5-yl}-2-bromobenzyl acetate
収率 37.6%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒2 回HCID 15413tert-Butyl methyl ether溶媒

実験手順

Under argon atmosphere, t-BuOK (0.36 g) was slowly added to 2-bromo-4-{[(trimethylsilyl)methyl]carbamothioyl}benzyl acetate (1.0 g) and iodomethane (0.45 g) in THF at −10° C., and the resultant mixture was stirred for 30 minutes at the same temperature. 2,6-bis(trifluoromethyl)-4-(3,3,3-trifluoroprop-1-en-2-yl)pyridine (1.1 g) was added to the reaction mixture, and then n-Bu4NF in THF (0.25 ml, 1M solution) was slowly added to the mixture at −10° C. under argon atmosphere. After stirring the resultant blend for 30 minutes at the same temperature, the blend was allowed to slowly warm to room temperature. The blend was stirred at room temperature overnight. The blend was diluted with t-BuOMe, and washed with 1N HCl and brine. The organic layer was dried over MgSO4. The solvent was evaporated under reduced pressure and the residue was purified by column chromatography to get the targeted product (0.58 g).

後処理

  1. stirringThe blend was stirred at room temperature overnight
  2. washwashed with 1N HCl and brine
  3. dry with materialThe organic layer was dried over MgSO4
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by column chromatography

出典と根拠

ORDレコード
ord-06f6a04c5b814e788dbacaad4f9dde3c
出典データセット
uspto-grants-2015_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09055749B2

反応ノート

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