Sodium hydride → 5-Bromo-2-(4-cyclohexyl-3-trifluoromethyl-benzyloxy)-pyridine

HRID 2100660

反応式

HRID 2100660 の反応式
[CH:1]1([C:7]2[CH:12]=[CH:11][C:10]([CH2:13][OH:14])=[CH:9][C:8]=2[C:15]([F:18])([F:17])[F:16])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[H-].[Na+].Cl[C:22]1[CH:27]=[CH:26][C:25]([Br:28])=[CH:24][N:23]=1.[NH4+].[Cl-]>CN(C=O)C>[Br:28][C:25]1[CH:26]=[CH:27][C:22]([O:14][CH2:13][C:10]2[CH:11]=[CH:12][C:7]([CH:1]3[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]3)=[C:8]([C:15]([F:16])([F:17])[F:18])[CH:9]=2)=[N:23][CH:24]=1

参加物

6

反応物 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 27344145-Bromo-2-chloropyridineHCID 22057748[4-Cyclohexyl-3-(trifluoromethyl)phenyl]methanol

生成物 1

HCID 688136965-Bromo-2-(4-cyclohexyl-3-trifluoromethyl-benzyloxy)-pyridine

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

反応条件

温度
0 °C

実験手順

To a solution of (4-cyclohexyl-3-trifluoromethyl-phenyl)-methanol (258 mg, 1.0 mmol) in DMF (7 mL) is added sodium hydride (60% in mineral oil, 60 mg, 1.5 mmol) at 0° C. and the reaction mixture is stirred at 0° C. for 30 minutes. After the addition of a solution of 2-chloro-5-bromopyridine (231 mg, 1.2 mmol) in DMF (3 mL), the reaction mixture is stirred at 0° C. for 1 h and at room temperature for 18 hours. The reaction mixture is poured into saturated aqueous NH4Cl and extracted with EtOAc. The combined extracts are washed with brine and dried over Na2SO4. After concentration, the residue is purified by silica gel chromatography (19:1 hexanes/EtOAc) to give 5-Bromo-2-(4-cyclohexyl-3-trifluoromethyl-benzyloxy)-pyridine.

後処理

  1. stirringthe reaction mixture is stirred at 0° C. for 1 h and at room temperature for 18 hours
  2. extractionextracted with EtOAc
  3. washThe combined extracts are washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationAfter concentration
  6. customthe residue is purified by silica gel chromatography (19:1 hexanes/EtOAc)

出典と根拠

ORDレコード
ord-1e51157896e94935842a7b9792f38800
出典データセット
uspto-grants-2009_08
特許番号
US07572811B2

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