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

HRID 1172667노트

반응식

HRID 1172667 반응식
[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

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 27788231-(Bromodifluoromethyl)-4-(difluoromethyl)benzene2회HCID 27828994-Methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazole-5-carbaldehydeHCID 5359967Indium

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-5e40d565316945fbbee7f95c63c46b54
출처 데이터셋
uspto-grants-2010_11
특허 번호
US07834030B2

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