Water → N-(5-Cyano-2-fluoro-3-hydroxy-6-methylbiphenyl-4-yl)-2,2-dimethylpropionamide

HRID 17322노트

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HRID 17322 반응식
ClCCl.[C:4]([C:6]1[C:7]([NH:22][C:23](=[O:28])[C:24]([CH3:27])([CH3:26])[CH3:25])=[C:8]([O:20]C)[C:9]([F:19])=[C:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:11]=1[CH3:12])#[N:5].BrB(Br)Br.O>[Cl-].[Na+].O>[C:4]([C:6]1[C:7]([NH:22][C:23](=[O:28])[C:24]([CH3:26])([CH3:25])[CH3:27])=[C:8]([OH:20])[C:9]([F:19])=[C:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:11]=1[CH3:12])#[N:5]

참가 물질

6

반응물 4

HCID 962WaterHCID 6344Dichloromethane2회HCID 25134Boron tribromideHCID 86630833N-(5-Cyano-2-fluoro-3-methoxy-6-methylbiphenyl-4-yl)-2,2-dimethylpropionamide

생성물 1

HCID 86630834N-(5-Cyano-2-fluoro-3-hydroxy-6-methylbiphenyl-4-yl)-2,2-dimethylpropionamide수율 88%

시약·촉매·용매 1

HCID 57417360Sodium chloride; water용매

반응 조건

온도
-78 °C

실험 절차

A dichloromethane (60 ml) solution of N-(5-cyano-2-fluoro-3-methoxy-6-methylbiphenyl-4-yl)-2,2-dimethylpropionamide (I-70) (2.02 g, 5.93 mmol) was cooled at −78° C., a dichloromethane solution of 1 N tribromoborane (17.8 ml, 17.8 mmol) was dropwise added, followed by stirring at −78° C. for 15 minutes. Afterwards, this was heated up to −12° C., and stirred for 30 minutes. The reaction liquid was put into cold water (100 ml), saturated brine (50 ml) was added, the intended product was extracted with ethyl acetate (300 ml×2). The organic layer was dried over anhydrous magnesium sulfate, concentrated under reduced pressure, the residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=5:1) to obtain the entitled compound (1.70 g, 88%) as a yellow solid.

후처리

  1. temperatureAfterwards, this was heated up to −12° C.
  2. stirringstirred for 30 minutes
  3. customThe reaction liquid
  4. additionwas added
  5. extractionthe intended product was extracted with ethyl acetate (300 ml×2)
  6. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customthe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=5:1)

출처 및 근거

ORD 기록
ord-1927bafe632e4646ac4a4679308e61e9
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07737166B2

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