Methyl iodide → Methyl 8-bromo-1,6-naphthyridine-2-carboxylate

HRID 1180565Notes

Reaction equation

HRID 1180565 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([C:12]([OH:14])=[O:13])[CH:8]=[CH:7]2.[C:15](=O)([O-])[O-].[Cs+].[Cs+].CI>CN(C=O)C.CCOC(C)=O>[CH3:15][O:13][C:12]([C:9]1[CH:8]=[CH:7][C:6]2[C:11](=[C:2]([Br:1])[CH:3]=[N:4][CH:5]=2)[N:10]=1)=[O:14]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 27610508-bromo-1,6-naphthyridine-2-carboxylic Acid

Product 1

HCID 11594176Methyl 8-bromo-1,6-naphthyridine-2-carboxylate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

8-Bromo-[1,6]naphthyridine-2-carboxylic acid methyl ester (2) is prepared by combining compound 1 (1 equiv.), cesium carbonate (1.1 equiv.) and methyl iodide (1.1 equiv.) in DMF (10 mL) and stirring for 16 hrs. at room temperature. The reaction is concentrated in vacuo to give a brown solid, which is dissolved in EtOAc (50 mL) and washed with water (2×50 mL). The EtOAc layer is dried over sodium sulfate, filtered, and concentrated in vacuo to afford a purple solid. The crude product is purified via silica gel chromatography (EtOAc) to yield (2) as a yellow solid, 65%, LC/MS (M+H) 269.0.

Workup

  1. custom8-Bromo-[1,6]naphthyridine-2-carboxylic acid methyl ester (2) is prepared
  2. customat room temperature
  3. concentrationThe reaction is concentrated in vacuo
  4. customto give a brown solid, which
  5. washwashed with water (2×50 mL)
  6. dry with materialThe EtOAc layer is dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customto afford a purple solid
  10. customThe crude product is purified via silica gel chromatography (EtOAc)

Sources & evidence

ORD record
ord-245a1a5eec6e48f0ad7842f349d930ea
Source dataset
uspto-grants-2007_10
Patent number
US07282506B2

Reaction notes

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