Water → {2-[1-(3,5-bis-trifluoromethyl-benzyl)-5-pyridin-4-yl-1H-[1,2,3]triazol-4-yl]-pyridin-3-yl}-(2-chloro-phenyl)-methanol

HRID 2251994노트

반응식

HRID 2251994 반응식
[H-].[H-].[H-].[H-].[Li+].[Al+3].[F:7][C:8]([F:47])([F:46])[C:9]1[CH:10]=[C:11]([CH:39]=[C:40]([C:42]([F:45])([F:44])[F:43])[CH:41]=1)[CH2:12][N:13]1[C:17]([C:18]2[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=2)=[C:16]([C:24]2[C:29]([C:30]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=3[Cl:38])=[O:31])=[CH:28][CH:27]=[CH:26][N:25]=2)[N:15]=[N:14]1.O>C1COCC1>[F:47][C:8]([F:7])([F:46])[C:9]1[CH:10]=[C:11]([CH:39]=[C:40]([C:42]([F:43])([F:45])[F:44])[CH:41]=1)[CH2:12][N:13]1[C:17]([C:18]2[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=2)=[C:16]([C:24]2[C:29]([CH:30]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=3[Cl:38])[OH:31])=[CH:28][CH:27]=[CH:26][N:25]=2)[N:15]=[N:14]1

참가 물질

5

반응물 3

HCID 962WaterHCID 9916461TradipitantHCID 21226445Aluminium lithium hydride

생성물 1

HCID 10175299{2-[1-(3,5-bis-trifluoromethyl-benzyl)-5-pyridin-4-yl-1H-[1,2,3]triazol-4-yl]-pyridin-3-yl}-(2-chloro-phenyl)-methanol수율 69%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

Add LiAlH4 (2.6 mL, 2.6 mmol, 1.0 M in THF) dropwise to a stirred solution of {2-[1-(3,5-bis-trifluoromethyl-benzyl)-5-pyridin-4-yl-1H-[1,2,3]triazol-4-yl]-pyridin-3-yl}-(2-chloro-phenyl)-methanone (1.28 g, 2.18 mmol) in THF (20 mL, anhydrous) at RT. After 15 min, add water (2.6 mL) dropwise with rapid stirring to quench. Add 1N NaOH solution (2.6 mL) dropwise, followed by dropwise addition of water (7.8 mL). Filter out solids and rinse with THF. Concentrate, dissolve in CH2Cl2, wash with saturated NaHCO3 solution (2×), dry over MgSO4 and concentrate. Purify the solid by flash chromatography on silica gel eluting with 0-15% ACN/Et2O to afford the title compound (882 mg, 69%); MS(IS) 590 (M+1); TLC: Rf=0.32 (7.5% EtOH/CHCl3).

후처리

  1. customto quench
  2. additionAdd 1N NaOH solution (2.6 mL) dropwise
  3. additionfollowed by dropwise addition of water (7.8 mL)
  4. filtrationFilter out solids
  5. washrinse with THF
  6. concentrationConcentrate
  7. dissolutiondissolve in CH2Cl2
  8. washwash with saturated NaHCO3 solution (2×)
  9. dry with materialdry over MgSO4
  10. concentrationconcentrate
  11. customPurify the solid by flash chromatography on silica gel eluting with 0-15% ACN/Et2O

출처 및 근거

ORD 기록
ord-4e666f0fbc7d413b9c50ebc4b5ca6971
출처 데이터셋
uspto-grants-2008_01
특허 번호
US07320994B2

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