Morpholine → Methyl 2-methyl-2-(5-morpholino-3-nitropyridin-2-yl)propanoate

HRID 1618535ノート

反応式

HRID 1618535 の反応式
Br[C:2]1[CH:3]=[C:4]([N+:15]([O-:17])=[O:16])[C:5]([C:8]([CH3:14])([CH3:13])[C:9]([O:11][CH3:12])=[O:10])=[N:6][CH:7]=1.[NH:18]1[CH2:23][CH2:22][O:21][CH2:20][CH2:19]1.CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C.CC(C)([O-])C.[Na+]>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH3:13][C:8]([C:5]1[C:4]([N+:15]([O-:17])=[O:16])=[CH:3][C:2]([N:18]2[CH2:23][CH2:22][O:21][CH2:20][CH2:19]2)=[CH:7][N:6]=1)([CH3:14])[C:9]([O:11][CH3:12])=[O:10]

参加物

7

反応物 4

HCID 8083MorpholineHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 23676156Sodium t-butoxideHCID 672852172-Pyridineacetic acid, 5-bromo-alpha,alpha-dimethyl-3-nitro-, methyl ester

生成物 1

HCID 67285292Methyl 2-methyl-2-(5-morpholino-3-nitropyridin-2-yl)propanoate

試薬・触媒・溶媒 2

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 1140Toluene溶媒

実験手順

A stirred mixture of methyl 2-(5-bromo-3-nitropyridin-2-yl)-2-methylpropanoate (1.2 g, 3.96 mmol), morpholine (0.34 mL, 3.96 mmol), Pd2dba3 (181 mg, 0.20 mmol), XPhos (189 mg, 0.40 mmol) and sodium tert-butoxide (1.1 g, 11.88 mmol) in toluene (30 mL) was heated at reflux for two h. After this time the reaction was cooled to rt and partitioned between EtOAc (300 mL) and water (100 mL). The separated organic layer was dried over MgSO4, filtered and evaporated in vacuo. Column chromatography gave methyl 2-methyl-2-(5-morpholino-3-nitropyridin-2-yl)propanoate as a yellow oil.

後処理

  1. temperaturewas heated
  2. temperatureat reflux for two h
  3. custompartitioned between EtOAc (300 mL) and water (100 mL)
  4. dry with materialThe separated organic layer was dried over MgSO4
  5. filtrationfiltered
  6. customevaporated in vacuo

出典と根拠

ORDレコード
ord-ae509e17941d44298cc8f7580b9cc086
出典データセット
uspto-grants-2014_07
特許番号
US08765940B2

反応ノート

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