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

HRID 925271노트

반응식

HRID 925271 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-83d0875bf4c34fb4a0ac369c643f7d3a
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09284286B2

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