Potassium Carbonate → 4-[[3,3-Difluoro-3-(4-fluorophenyl)-propyl]sulfanyl]-2-methyl-thiazole-5-carboxylic acid ethyl ester

HRID 925277노트

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HRID 925277 반응식
[CH2:1]([O:3][C:4]([C:6]1[S:10][C:9]([CH3:11])=[N:8][C:7]=1[SH:12])=[O:5])[CH3:2].Br[CH2:14][CH2:15][C:16]([C:19]1[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=1)([F:18])[F:17].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:1]([O:3][C:4]([C:6]1[S:10][C:9]([CH3:11])=[N:8][C:7]=1[S:12][CH2:14][CH2:15][C:16]([F:18])([F:17])[C:19]1[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=1)=[O:5])[CH3:2]

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 15077130Ethyl 2-methyl-4-sulfanyl-1,3-thiazole-5-carboxylateHCID 671338221-(3-Bromo-1,1-difluoropropyl)-4-fluorobenzene

생성물 1

HCID 867201714-[[3,3-Difluoro-3-(4-fluorophenyl)-propyl]sulfanyl]-2-methyl-thiazole-5-carboxylic acid ethyl ester수율 56%

시약·촉매·용매 1

HCID 180Acetone용매

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온도
80 °C

실험 절차

To a solution of give 4-mercapto-2-methyl-thiazole-5-carboxylic acid ethyl ester (0.58 g, 2.83 mmol) in acetone (10 ml) are added 1-(3-bromo-1,1-difluoro-propyl)-4-fluoro-benzene (synthesized according to the methods described in sections a) to e) of example 1) (0.72 g, 2.83 mmol) and potassium carbonate (0.78 g, 5.66 mmol) an the mixture is heated at 80° C. for 16 h. Acetone is evaporated, diluted with water (40 ml) and extracted with EtOAc (3×30 ml). The crude product is purified by column chromatography (silica gel, 10% EtOAc/hexane) yielding 4-[[3,3-difluoro-3-(4-fluorophenyl)-propyl]sulfanyl]-2-methyl-thiazole-5-carboxylic acid ethyl ester (0.6 g, 1.6 mmol, 56%).

후처리

  1. customsynthesized
  2. customAcetone is evaporated
  3. additiondiluted with water (40 ml)
  4. extractionextracted with EtOAc (3×30 ml)
  5. customThe crude product is purified by column chromatography (silica gel, 10% EtOAc/hexane)

출처 및 근거

ORD 기록
ord-70b467d4f7d1439c82e361e80e93ca53
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09284286B2

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