Sodium Carbonate → 7,8-Dibromo-2-methoxy-[1,5]naphthyridine

HRID 1422921Notes

Reaction equation

HRID 1422921 reaction equation
P(Br)(Br)[Br:2].[Br:5][C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1O)=[N:13][C:12]([O:17][CH3:18])=[CH:11][CH:10]=2.C(=O)([O-])[O-].[Na+].[Na+]>CN(C)C=O>[Br:5][C:6]1[C:15]([Br:2])=[C:14]2[C:9]([CH:10]=[CH:11][C:12]([O:17][CH3:18])=[N:13]2)=[N:8][CH:7]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 24614Phosphorus tribromideHCID 178487833HCID 178487833, compound

Product 1

HCID 672578837,8-Dibromo-2-methoxy-[1,5]naphthyridineYield 80.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Phosphorus tribromide (140 mg, 0.53 mmol, 1.3 eq) is added at 0° C. to a stirred suspension of 3-bromo-6-methoxy-[1,5]naphthyridin-4-ol (100 mg, 0.39 mmol, 1.0 eq) in N,N-dimethylformamide (1 mL). After 2 hours stirring at room temperature, the reaction mixture is poured into saturated sodium carbonate aqueous solution (50 mL). The resulting suspension is filtered and the cake is washed with water and methanol to afford 7,8-dibromo-2-methoxy-[1,5]naphthyridine as a white solid (100 mg, 80% yield).

Workup

  1. filtrationThe resulting suspension is filtered
  2. washthe cake is washed with water and methanol

Sources & evidence

ORD record
ord-c895db0e41e340c68c0c93aaee00e6ca
Source dataset
uspto-grants-2015_01
Patent number
US08927541B2

Reaction notes

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