Potassium Hydroxide → (5-(Hydroxy-[5-(2-morpholin-4-yl-ethoxy)-1H-pyrrolo[2,3-b]pyridin-3-yl]-methyl}-pyridin-2-yl)-(4-trifluoromethyl-benzyl)-carbamic acid tert-butyl ester

HRID 2387271ノート

反応式

HRID 2387271 の反応式
[C:1]([O:5][C:6](=[O:27])[N:7]([C:19]1[CH:24]=[CH:23][C:22]([CH:25]=[O:26])=[CH:21][N:20]=1)[CH2:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:11][CH:10]=1)([CH3:4])([CH3:3])[CH3:2].[N:28]1([CH2:34][CH2:35][O:36][C:37]2[CH:38]=[C:39]3[CH:45]=[CH:44][NH:43][C:40]3=[N:41][CH:42]=2)[CH2:33][CH2:32][O:31][CH2:30][CH2:29]1.[OH-].[K+]>CO>[C:1]([O:5][C:6](=[O:27])[N:7]([C:19]1[CH:24]=[CH:23][C:22]([CH:25]([OH:26])[C:45]2[C:39]3[C:40](=[N:41][CH:42]=[C:37]([O:36][CH2:35][CH2:34][N:28]4[CH2:33][CH2:32][O:31][CH2:30][CH2:29]4)[CH:38]=3)[NH:43][CH:44]=2)=[CH:21][N:20]=1)[CH2:8][C:9]1[CH:10]=[CH:11][C:12]([C:15]([F:16])([F:17])[F:18])=[CH:13][CH:14]=1)([CH3:4])([CH3:2])[CH3:3]

参加物

5

反応物 3

HCID 14797Potassium HydroxideHCID 595932655-(2-Morpholin-4-yl-ethoxy)-1H-pyrrolo[2,3-b]pyridineHCID 59593275(5-Formyl-pyridin-2-yl)-(4-trifluoromethyl-benzyl)-carbamic acid tert-butyl ester

生成物 1

HCID 59593292(5-(Hydroxy-[5-(2-morpholin-4-yl-ethoxy)-1H-pyrrolo[2,3-b]pyridin-3-yl]-methyl}-pyridin-2-yl)-(4-trifluoromethyl-benzyl)-carbamic acid tert-butyl ester収率 40%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

A mixture of (5-Formyl-pyridin-2-yl)-(4-trifluoromethyl-benzyl)-carbamic acid tert-butyl ester (23, 315 mg, 0.828 mmol), 5-(2-morpholin-4-yl-ethoxy)-1-pyrrolo[2,3-b]pyridine (20, 205 mg, 0.829 mmol, prepared as described in Example 14), and potassium hydroxide (70 mg, 1 mmol) in methanol (25 mL) was stirred at room temperature overnight. The reaction mixture was poured into ice water, extracted with ethyl acetate, washed with brine, and dried over sodium sulfate. After removal of solvent, the residue was purified by silica gel column chromatography eluting with methanol in dichloromethane to provide the compound as a yellow solid (24, 0.2 g, 40%). MS (ESI) [M+H+]+=628.42.

後処理

  1. extractionextracted with ethyl acetate
  2. washwashed with brine
  3. dry with materialdried over sodium sulfate
  4. customAfter removal of solvent
  5. customthe residue was purified by silica gel column chromatography
  6. washeluting with methanol in dichloromethane

出典と根拠

ORDレコード
ord-2eafb44111c5483783471a9d1339000d
出典データセット
uspto-grants-2012_09
特許番号
US08268858B2

反応ノート

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