Water → Methyl 8-(benzyloxy)-5-bromo-1,6-naphthyridine-7-carboxylate

HRID 455289Notes

Reaction equation

HRID 455289 reaction equation
[CH2:1](Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:9][C:10]1[N:19]=[C:18]([C:20]([O:22][CH3:23])=[O:21])[C:17]([OH:24])=[C:16]2[C:11]=1[CH:12]=[CH:13][CH:14]=[N:15]2.C(=O)([O-])[O-].[Cs+].[Cs+].O>CN(C=O)C.C(OCC)(=O)C>[CH2:1]([O:24][C:17]1[C:18]([C:20]([O:22][CH3:23])=[O:21])=[N:19][C:10]([Br:9])=[C:11]2[C:16]=1[N:15]=[CH:14][CH:13]=[CH:12]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 10796Cesium carbonateHCID 22343006Methyl 5-bromo-8-hydroxy-1,6-naphthyridine-7-carboxylate

Product 1

HCID 71699854Methyl 8-(benzyloxy)-5-bromo-1,6-naphthyridine-7-carboxylate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Benzyl bromide (2.53 ml, 21.2 mmol) was added to a mixture of methyl 5-bromo-8-hydroxy-1,6-naphthyridine-7-carboxylate (3.0 g; 10.6 mmol) and cesium carbonate (6.9 g; 21.2 mmol) in DMF (30 ml), under stirring at room temperature. The reaction mixture was stirred at room temperature for 12 hours. Water and ethyl acetate were added. The organic phase was separated, washed with water and with a saturated NaCl solution. The organic phase was dried, filtered and concentrated to dryness. The crude material was purified by flash chromatography column over silica gel (eluting with a gradient hexane-ethyl acetate 10:1 to 2:1).

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 12 hours
  2. customThe organic phase was separated
  3. washwashed with water and with a saturated NaCl solution
  4. customThe organic phase was dried
  5. filtrationfiltered
  6. concentrationconcentrated to dryness
  7. customThe crude material was purified by flash chromatography column over silica gel (
  8. washeluting with a gradient hexane-ethyl acetate 10:1 to 2:1)

Sources & evidence

ORD record
ord-36a50744fcce45e69467755e5daa379a
Source dataset
uspto-grants-2013_07
Patent number
US08497270B2

Reaction notes

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