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Toluene → 1-(2-Cyclopropyl-1-methyl-1H-benzimidazol-6-yl)-4-((2-(trifluoromethyl)-1,3-thiazol-4-yl)methoxy)pyridin-2(1H)-one

HRID 2203093
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HRID 2203093 반응식
Br[C:2]1[CH:7]=[CH:6][N:5]([C:8]2[CH:9]=[CH:10][C:11]3[N:15]=[C:14]([CH:16]4[CH2:18][CH2:17]4)[N:13]([CH3:19])[C:12]=3[CH:20]=2)[C:4](=[O:21])[CH:3]=1.[F:22][C:23]([F:32])([F:31])[C:24]1[S:25][CH:26]=[C:27]([CH2:29][OH:30])[N:28]=1.C1(C)C=CC=CC=1.CC(C)([O-])C.[K+]>O>[CH:16]1([C:14]2[N:13]([CH3:19])[C:12]3[CH:20]=[C:8]([N:5]4[CH:6]=[CH:7][C:2]([O:30][CH2:29][C:27]5[N:28]=[C:24]([C:23]([F:32])([F:31])[F:22])[S:25][CH:26]=5)=[CH:3][C:4]4=[O:21])[CH:9]=[CH:10][C:11]=3[N:15]=2)[CH2:18][CH2:17]1
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참가 물질

6

반응물 4

HCID 1140TolueneHCID 20079604[2-(Trifluoromethyl)-1,3-thiazol-4-yl]methanolHCID 23665647Potassium tert-butoxideHCID 896908634-Bromo-1-(2-cyclopropyl-1-methyl-1H-benzimidazol-6-yl)pyridin-2(1H)-one

생성물 1

HCID 897022641-(2-Cyclopropyl-1-methyl-1H-benzimidazol-6-yl)-4-((2-(trifluoromethyl)-1,3-thiazol-4-yl)methoxy)pyridin-2(1H)-one수율 22.4%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

To a mixture of 4-bromo-1-(2-cyclopropyl-1-methyl-1H-benzimidazol-6-yl)pyridin-2(1H)-one (100 mg), (2-(trifluoromethyl)thiazol-4-yl)methanol (80 mg) and toluene (5 ml) was added potassium tert-butoxide (98 mg) at 100° C., and the mixture was stirred at the same temperature overnight. The mixture was poured into water, and extracted with EtOAc. The extract was washed with brine, dried over MgSO4, concentrated in vacuo, and purified by NH silica gel column chromatography (hexane/EtOAc) to give the title compound (29.0 mg) as a white solid.

후처리

  1. extractionextracted with EtOAc
  2. washThe extract was washed with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. custompurified by NH silica gel column chromatography (hexane/EtOAc)

출처 및 근거

ORD 기록
ord-ef3451a9f6744524967fa48bbf7f0f20
출처 데이터셋
uspto-grants-2016_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09365540B2

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