Water → 8-Bromo-7-chloro-2-methoxy-1,5-naphthyridine

HRID 15300Notes

Reaction equation

HRID 15300 reaction equation
[Cl:1][C:2]1[C:11](=O)[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([O:13][CH3:14])[N:9]=2)[NH:4][CH:3]=1.P(Br)(Br)[Br:16].O.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[Br:16][C:11]1[C:2]([Cl:1])=[CH:3][N:4]=[C:5]2[C:10]=1[N:9]=[C:8]([O:13][CH3:14])[CH:7]=[CH:6]2

Participants

7

Reactant 5

HCID 962Water2×HCID 11430Potassium CarbonateHCID 24614Phosphorus tribromideHCID 574188103-Chloro-6-methoxy-[1,5]naphthyridin-4-olHCID 178487877HCID 178487877, compound

Product 1

HCID 513582238-Bromo-7-chloro-2-methoxy-1,5-naphthyridineYield 88%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
10 °C

Procedure

To a solution of 3-chloro-6-(methyloxy)-1,5-naphthyridin-4(1H)-one (3-chloro-6-(methyloxy)-1,5-naphthyridin-4-ol, for a synthesis see WO2004058144, Example 1(a) (5.1 g, 24.28 mmol) in DMF (50 ml) at 0° C. was added phosphorous tribromide dropwise (2.77 ml, 29.1 mmol) keeping the internal temperature below 20° C. The reaction mixture was then stirred at 10° C. for 0.5 h and then at 25° C. for 1 h. The mixture was then poured on 200 ml of water and the water basified to neutral pH with potassium carbonate. The solid formed was filtered off, washed with water and dried in the oven and then in the desiccator to afford the desired compound (5.8 g, 88%).

Workup

  1. customat 0° C.
  2. customthe internal temperature below 20° C
  3. waitat 25° C. for 1 h
  4. customThe solid formed
  5. filtrationwas filtered off
  6. washwashed with water
  7. customdried in the oven

Sources & evidence

ORD record
ord-e4684de893ad4d35bc1afb5e6c40bf97
Source dataset
uspto-grants-2010_06
Patent number
US07732461B2

Reaction notes

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