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 1952037ノート

反応式

HRID 1952037 の反応式
[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]

参加物

6

反応物 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

生成物 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

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

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%).

後処理

  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%)

出典と根拠

ORDレコード
ord-bd8fd22dd8074fc286ea97b4043683a8
出典データセット
uspto-grants-2013_03
特許番号
US08404700B2

反応ノート

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