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

HRID 925277ノート

反応式

HRID 925277 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

反応条件

温度
80 °C

実験手順

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%).

後処理

  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)

出典と根拠

ORDレコード
ord-70b467d4f7d1439c82e361e80e93ca53
出典データセット
uspto-grants-2016_03
特許番号
US09284286B2

反応ノート

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