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 472046노트

반응식

HRID 472046 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-9cd6407371f74895aacc8481c2fbb360
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08633193B2

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