Sodium borohydride → 1-[1-(2-chloro-6-ethyl-pyrimidin-4-yl)-5-(2,6-dimethyl-phenyl)-1H-pyrrolo[2,3-c]pyridin-3-yl]-2-ethyl-butan-1-ol

HRID 602549노트

반응식

HRID 602549 반응식
[Cl:1][C:2]1[N:7]=[C:6]([N:8]2[C:12]3=[CH:13][N:14]=[C:15]([C:17]4[C:22]([CH3:23])=[CH:21][CH:20]=[CH:19][C:18]=4[CH3:24])[CH:16]=[C:11]3[C:10]([C:25](=[O:31])[CH:26]([CH2:29][CH3:30])[CH2:27][CH3:28])=[CH:9]2)[CH:5]=[C:4]([CH2:32][CH3:33])[N:3]=1.[BH4-].[Na+]>C(O)C.O>[Cl:1][C:2]1[N:7]=[C:6]([N:8]2[C:12]3=[CH:13][N:14]=[C:15]([C:17]4[C:22]([CH3:23])=[CH:21][CH:20]=[CH:19][C:18]=4[CH3:24])[CH:16]=[C:11]3[C:10]([CH:25]([OH:31])[CH:26]([CH2:27][CH3:28])[CH2:29][CH3:30])=[CH:9]2)[CH:5]=[C:4]([CH2:32][CH3:33])[N:3]=1

참가 물질

4

반응물 2

HCID 4311764Sodium borohydrideHCID 866240811-[1-(2-chloro-6-ethyl-pyrimidin-4-yl)-5-(2,6-dimethyl-phenyl)-1H-pyrrolo[2,3-c]pyridin-3-yl]-2-ethyl-butan-1-one

생성물 1

HCID 866240821-[1-(2-chloro-6-ethyl-pyrimidin-4-yl)-5-(2,6-dimethyl-phenyl)-1H-pyrrolo[2,3-c]pyridin-3-yl]-2-ethyl-butan-1-ol

시약·촉매·용매 1

HCID 19096565Water ethanol용매

실험 절차

To a solution of 1-[1-(2-chloro-6-ethyl-pyrimidin-4-yl)-5-(2,6-dimethyl-phenyl)-1H-pyrrolo[2,3-c]pyridin-3-yl]-2-ethyl-butan-1-one (150 mg, 0.32 mmol) in a (4:1) mixture EtOH—H2O (4 mL) at −30° C., NaBH4 (70 mg, 1.8 mmol) is added, and the mixture is allowed gradually warm up to room temperature at which the reaction is maintained for 2 h. The mixture is concentrated under reduced pressure, and an aqueous saturated Rochelle's salt solution (10 mL) is added. The resulting suspension is stirred at room temperature for 1 h, and the product is extracted with DCM. The obtained solution is washed with brine, dried (Na2SO4), and concentrated under reduced pressure. Chromatography of the residue on silica gel (hexane-EtOAc, 1:1) gives 1-[1-(2-chloro-6-ethyl-pyrimidin-4-yl)-5-(2,6-dimethyl-phenyl)-1H-pyrrolo[2,3-c]pyridin-3-yl]-2-ethyl-butan-1-ol as colorless oil.

후처리

  1. temperatureis maintained for 2 h
  2. concentrationThe mixture is concentrated under reduced pressure
  3. additionan aqueous saturated Rochelle's salt solution (10 mL) is added
  4. extractionthe product is extracted with DCM
  5. washThe obtained solution is washed with brine
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-90008864445f496aa8d8ada530e43d57
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07906528B2

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