Water → 6-bromo-N-((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-1-(2-methylallyl)-1H-pyrazolo[3,4-b]pyridine-4-carboxamide

HRID 1909199ノート

反応式

HRID 1909199 の反応式
[Br:1][C:2]1[CH:3]=[C:4]([C:11]([NH:13][CH2:14][C:15]2[C:16](=[O:23])[NH:17][C:18]([CH3:22])=[CH:19][C:20]=2[CH3:21])=[O:12])[C:5]2[CH:10]=[N:9][NH:8][C:6]=2[N:7]=1.C([O-])([O-])=O.[K+].[K+].Cl[CH:31]=[C:32]([CH3:34])[CH3:33].O>CN(C=O)C.CO.C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]([C:11]([NH:13][CH2:14][C:15]2[C:16](=[O:23])[NH:17][C:18]([CH3:22])=[CH:19][C:20]=2[CH3:21])=[O:12])[C:5]2[CH:10]=[N:9][N:8]([CH2:33][C:32]([CH3:34])=[CH2:31])[C:6]=2[N:7]=1

参加物

7

反応物 4

HCID 962WaterHCID 105551-Propene, 1-chloro-2-methyl-HCID 11430Potassium CarbonateHCID 867034116-bromo-N-((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-1H-pyrazolo[3,4-b]pyridine-4-carboxamide

生成物 1

HCID 867034136-bromo-N-((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-1-(2-methylallyl)-1H-pyrazolo[3,4-b]pyridine-4-carboxamide収率 46.5%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 21226129Dichloromethane methanol溶媒

反応条件

温度
80 °C

実験手順

To a stirred solution of 6-bromo-N-((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-1H-pyrazolo[3,4-b]pyridine-4-carboxamide (0.4 g, 1.0 mmol) in DMF (4 mL), K2CO3 (0.152 g, 1.10 mmol) and 3 chloro-2-methylpropene (0.115 g, 1.27 mmol) were added. Resulting reaction mixture was stirred at 80° C. for 2 h. On completion of reaction, water was added to it and extraction was carried out using 20% MeOH/DCM; the combined organic layers were washed with water, brine and dried over anhydrous Na2SO4. Solvent was removed under reduced pressure and residue was purified by silica gel column chromatography to obtain the desired intermediate (0.2 g, 43.8%).

後処理

  1. customResulting
  2. customreaction mixture
  3. additionwas added to it and extraction
  4. washthe combined organic layers were washed with water, brine
  5. dry with materialdried over anhydrous Na2SO4
  6. customSolvent was removed under reduced pressure and residue
  7. customwas purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-c3e5fa69b5e144a988e1a8398d1803fb
出典データセット
uspto-grants-2013_12
特許番号
US08598167B1

反応ノート

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