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

HRID 2100660

반응식

HRID 2100660 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

반응 조건

온도
0 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-1e51157896e94935842a7b9792f38800
출처 데이터셋
uspto-grants-2009_08
특허 번호
US07572811B2

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