Ethyl 3-bromo-2-oxobutanoate → Methyl 3-methylimidazo[2,1-f][1,6]naphthyridine-2-carboxylate

HRID 1615696Notes

Reaction equation

HRID 1615696 reaction equation
[N:1]1[C:10]2[CH:9]=[CH:8][N:7]=[C:6]([NH2:11])[C:5]=2[CH:4]=[CH:3][CH:2]=1.Br[CH:13]([CH3:21])[C:14](=O)[C:15]([O:17][CH2:18]C)=[O:16]>C1COCC1>[CH3:21][C:13]1[N:7]2[C:6]([C:5]3[CH:4]=[CH:3][CH:2]=[N:1][C:10]=3[CH:9]=[CH:8]2)=[N:11][C:14]=1[C:15]([O:17][CH3:18])=[O:16]

Participants

4

Reactant 2

HCID 11117285Ethyl 3-bromo-2-oxobutanoateHCID 292496221,6-Naphthyridin-5-amine

Product 1

HCID 70115494Methyl 3-methylimidazo[2,1-f][1,6]naphthyridine-2-carboxylateYield 63.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1,6-naphthyridin-5-amine (700 mg, 4.83 mmol) in THF (25 mL) was added ethyl 3-bromo-2-oxobutanoate (1.51 g, 7.24 mmol). The mixture was stirred at reflux for 36 h. Then the mixture was concentrated under reduced pressure, and purified by column chromatography to give the product as a yellow solid (740 mg, 60% yield). ESI MS: m/z 256.1 [M+H]+.

Workup

  1. temperatureat reflux for 36 h
  2. concentrationThen the mixture was concentrated under reduced pressure
  3. custompurified by column chromatography

Sources & evidence

ORD record
ord-49478f5b50b94c86b2c2a1940f2864cf
Source dataset
uspto-grants-2014_07
Patent number
US08765760B2

Reaction notes

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