Cesium carbonate → 3-[[3,3-Difluoro-3-(4-fluorophenyl)-propyl]sulfanyl]-N-(3-methyl-butyl)-pyridine-2-carboxylic acid amide

HRID 925265노트

반응식

HRID 925265 반응식
[F:1][C:2]([F:13])([C:6]1[CH:11]=[CH:10][C:9]([F:12])=[CH:8][CH:7]=1)[CH2:3][CH2:4][SH:5].F[C:15]1[C:16]([C:21]([NH:23][CH2:24][CH2:25][CH:26]([CH3:28])[CH3:27])=[O:22])=[N:17][CH:18]=[CH:19][CH:20]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[F:13][C:2]([F:1])([C:6]1[CH:11]=[CH:10][C:9]([F:12])=[CH:8][CH:7]=1)[CH2:3][CH2:4][S:5][C:15]1[C:16]([C:21]([NH:23][CH2:24][CH2:25][CH:26]([CH3:28])[CH3:27])=[O:22])=[N:17][CH:18]=[CH:19][CH:20]=1

참가 물질

5

반응물 3

HCID 10796Cesium carbonateHCID 867201623,3-Difluoro-3-(4-fluorophenyl)-propane-1-thiolHCID 867201633-fluoro-N-(3-methyl-butyl)-pyridine-2-carboxylic acid amide

생성물 1

HCID 762874063-[[3,3-Difluoro-3-(4-fluorophenyl)-propyl]sulfanyl]-N-(3-methyl-butyl)-pyridine-2-carboxylic acid amide수율 41%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
90 °C

실험 절차

To a solution of 3,3-difluoro-3-(4-fluorophenyl)-propane-1-thiol (0.19 g, 0.92 mmol) in DMF (5 ml) in sealed tube are added 3-fluoro-N-(3-methyl-butyl)-pyridine-2-carboxylic acid amide (0.19 g, 0.92 mmol) and cesium carbonate (1.50 g, 4.60 mmol). The reaction mixture is heated at 90° C. for 2 h. After completion of the reaction, the reaction mixture is poured onto ice-water, extracted with EtOAc (3×30 ml). The combined organic layers are washed with brine (50 ml), water (30 ml), dried over sodium sulfate and evaporated to dryness to yield the crude product, which is purified by column chromatography (silica gel, 30% EtOAc/hexane) affording 3-[[3,3-Difluoro-3-(4-fluorophenyl)-propyl]sulfanyl]-N-(3-methyl-butyl)-pyridine-2-carboxylic acid amide (example 3) (0.15 g, 0.37 mmol, 41%). [M+H]+ 397.1.

후처리

  1. customAfter completion of the reaction
  2. additionthe reaction mixture is poured onto ice-water
  3. extractionextracted with EtOAc (3×30 ml)
  4. washThe combined organic layers are washed with brine (50 ml), water (30 ml)
  5. dry with materialdried over sodium sulfate
  6. customevaporated to dryness
  7. customto yield the crude product, which
  8. customis purified by column chromatography (silica gel, 30% EtOAc/hexane)

출처 및 근거

ORD 기록
ord-b4e41457dbf64be0bb72c7a3d2f13bbb
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09284286B2

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