Triethylamine → 4-[[3,3-Difluoro-3-(4-fluorophenyl)-propyl]sulfanyl]-thiazole-5-carboxylic acid methyl ester

HRID 925271ノート

反応式

HRID 925271 の反応式
[CH3:1][O:2][C:3]([C:5]1[S:9][CH:8]=[N:7][C:6]=1[SH:10])=[O:4].C(N(CC)CC)C.Br[CH2:19][CH2:20][C:21]([C:24]1[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=1)([F:23])[F:22]>CN(C=O)C>[CH3:1][O:2][C:3]([C:5]1[S:9][CH:8]=[N:7][C:6]=1[S:10][CH2:19][CH2:20][C:21]([F:23])([F:22])[C:24]1[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=1)=[O:4]

参加物

5

反応物 3

HCID 8471TriethylamineHCID 671338221-(3-Bromo-1,1-difluoropropyl)-4-fluorobenzeneHCID 867201674-Mercapto-thiazole-5-carboxylic acid methyl ester

生成物 1

HCID 867201694-[[3,3-Difluoro-3-(4-fluorophenyl)-propyl]sulfanyl]-thiazole-5-carboxylic acid methyl ester収率 56%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

4-Mercapto-thiazole-5-carboxylic acid methyl ester (0.41 g, 2.16 mmol) is dissolved in DMF (6 ml) and triethylamine (0.45 ml, 3.24 mmol) and 1-(3-bromo-1,1-difluoro-propyl)-4-fluoro-benzene (synthesized according to the methods described in sections a) to e) of example 1) (0.55 g, 2.16 mmol) are added successively. The resulting mixture is stirred at RT for 16 h. After completion of the reaction, the mixture is poured onto water (20 ml) and extracted with EtOAc (3×30 ml). The combined organic layers are washed with brine (20 ml), dried over sodium sulfate and concentrated to dryness. The crude is purified by column chromatography (silica gel, 20% EtOAc/hexane) yielding 4-[[3,3-difluoro-3-(4-fluorophenyl)-propyl]sulfanyl]-thiazole-5-carboxylic acid methyl ester (0.42 g, 1.2 mmol, 56%).

後処理

  1. additionare added successively
  2. customAfter completion of the reaction
  3. additionthe mixture is poured onto water (20 ml)
  4. extractionextracted with EtOAc (3×30 ml)
  5. washThe combined organic layers are washed with brine (20 ml)
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated to dryness
  8. customThe crude is purified by column chromatography (silica gel, 20% EtOAc/hexane)

出典と根拠

ORDレコード
ord-83d0875bf4c34fb4a0ac369c643f7d3a
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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