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

HRID 868998Notes

Reaction equation

HRID 868998 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]>O1CCCC1>[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 tetrahydrofuran (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 740 mg of the product as a yellow solid. MS (ESI): 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-47f326fe631b4ae7b62a641475acc662
Source dataset
uspto-grants-2015_03
Patent number
US08969349B2

Reaction notes

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