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

HRID 17322ノート

反応式

HRID 17322 の反応式
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]

参加物

6

反応物 4

HCID 962WaterHCID 6344Dichloromethane2 回HCID 25134Boron tribromideHCID 86630833N-(5-Cyano-2-fluoro-3-methoxy-6-methylbiphenyl-4-yl)-2,2-dimethylpropionamide

生成物 1

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

試薬・触媒・溶媒 1

HCID 57417360Sodium chloride; water溶媒

反応条件

温度
-78 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-1927bafe632e4646ac4a4679308e61e9
出典データセット
uspto-grants-2010_06
特許番号
US07737166B2

反応ノート

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