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

HRID 1618535노트

반응식

HRID 1618535 반응식
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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 1140Toluene용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-ae509e17941d44298cc8f7580b9cc086
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08765940B2

반응 노트

불러오는 중…