Methanol → (5-[(5-Bromo-1H-pyrrolo[2,3-b]pyridin-3-yl)-hydroxy-methyl]-pyridin-2-yl)-(4-chloro-benzyl)-carbamic acid tert-butyl ester

HRID 1256732노트

반응식

HRID 1256732 반응식
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[N:9][CH:10]=1)[NH:7][CH:6]=[CH:5]2.CO.[C:13]([O:17][C:18](=[O:36])[N:19]([CH2:28][C:29]1[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][CH:30]=1)[C:20]1[CH:25]=[CH:24][C:23]([CH:26]=[O:27])=[CH:22][N:21]=1)([CH3:16])([CH3:15])[CH3:14].[OH-].[K+]>O>[C:13]([O:17][C:18](=[O:36])[N:19]([C:20]1[CH:25]=[CH:24][C:23]([CH:26]([C:5]2[C:4]3[C:8](=[N:9][CH:10]=[C:2]([Br:1])[CH:3]=3)[NH:7][CH:6]=2)[OH:27])=[CH:22][N:21]=1)[CH2:28][C:29]1[CH:30]=[CH:31][C:32]([Cl:35])=[CH:33][CH:34]=1)([CH3:16])([CH3:14])[CH3:15]

참가 물질

6

반응물 4

HCID 887MethanolHCID 14797Potassium HydroxideHCID 103079325-bromo-1H-pyrrolo[2,3-b]pyridineHCID 59593313(4-Chloro-benzyl)-(5-formyl-pyridin-2-yl)-carbamic acid tert-butyl ester

생성물 1

HCID 59593354(5-[(5-Bromo-1H-pyrrolo[2,3-b]pyridin-3-yl)-hydroxy-methyl]-pyridin-2-yl)-(4-chloro-benzyl)-carbamic acid tert-butyl ester

시약·촉매·용매 1

HCID 962Water용매

실험 절차

To 5-bromo-7-azaindole (44, 198.0 mg, 1.01 mmol) in methanol (30.0 mL, 0.741 mol) were added (4-Chloro-benzyl)-(5-formyl-pyridin-2-yl)-carbamic acid tert-butyl ester (43, 355.0 mg, 1.02 mmol) and potassium hydroxide (80.0 mg, 1.42 mmol). The reaction was stirred at room temperature 48 hours. The reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate, concentrated and purified by silica gel column chromatography eluting with 8% methanol in dichloromethane to give compound (45, 200.0 mg, 36.8%).

후처리

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. custompurified by silica gel column chromatography
  6. washeluting with 8% methanol in dichloromethane
  7. customto give compound (45, 200.0 mg, 36.8%)

출처 및 근거

ORD 기록
ord-4f4f29d108c944ff99b59aa6025c278c
출처 데이터셋
uspto-grants-2013_06
특허 번호
US08461169B2

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