Hydrochloric Acid → 2-(4-Difluoromethyl-phenyl)-2,2-difluoro-1-[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-yl]-ethanol

HRID 1172667ノート

反応式

HRID 1172667 の反応式
[CH3:1][C:2]1[N:3]=[C:4]([C:9]2[CH:14]=[CH:13][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:11][CH:10]=2)[S:5][C:6]=1[CH:7]=[O:8].Br[C:20]([F:31])([F:30])[C:21]1[CH:26]=[CH:25][C:24]([CH:27]([F:29])[F:28])=[CH:23][CH:22]=1.[In].Cl>CN(C)C=O>[F:28][CH:27]([F:29])[C:24]1[CH:23]=[CH:22][C:21]([C:20]([F:31])([F:30])[CH:7]([C:6]2[S:5][C:4]([C:9]3[CH:10]=[CH:11][C:12]([C:15]([F:18])([F:16])[F:17])=[CH:13][CH:14]=3)=[N:3][C:2]=2[CH3:1])[OH:8])=[CH:26][CH:25]=1

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 27788231-(Bromodifluoromethyl)-4-(difluoromethyl)benzene2 回HCID 27828994-Methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazole-5-carbaldehydeHCID 5359967Indium

生成物 1

HCID 595563802-(4-Difluoromethyl-phenyl)-2,2-difluoro-1-[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-yl]-ethanol収率 37.4%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a solution of 1.0 g 4-Methyl-2-(4-trifluoromethyl-phenyl)-thiazole-5-carbaldehyde and 1.42 g 4-(bromodifluoromethyl)-1-(difluoromethyl)benzene in 10 ml dimethylformamide 508 mg Indium were added and the resulting suspension was stirred in an ultrasonic bath for twelve hours. Then additional 1.42 g 4-(bromodifluoromethyl)-1-(difluoromethyl)benzene and 508 mg Indium were added and the resulting suspension was stirred in an ultrasonic bath for additional twelve hours. Then 20 ml 1 N hydrochloric acid were added and the mixture stirred at room temperature for thirty minutes. The mixture was extracted three times with portions of 50 ml ethyl acetate. The combined organic layers were dried over MgSO4. The solvent was evaporated in vacuo. The resulting residue was purified by reversed phase HPLC to obtain 620 mg 2-(4-Difluoromethyl-phenyl)-2,2-difluoro-1-[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-yl]-ethanol as a colorless lyophilisate.

後処理

  1. stirringthe resulting suspension was stirred in an ultrasonic bath for additional twelve hours
  2. stirringthe mixture stirred at room temperature for thirty minutes
  3. extractionThe mixture was extracted three times with portions of 50 ml ethyl acetate
  4. dry with materialThe combined organic layers were dried over MgSO4
  5. customThe solvent was evaporated in vacuo
  6. customThe resulting residue was purified by reversed phase HPLC

出典と根拠

ORDレコード
ord-5e40d565316945fbbee7f95c63c46b54
出典データセット
uspto-grants-2010_11
特許番号
US07834030B2

反応ノート

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