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

HRID 1881723Notes

Reaction equation

HRID 1881723 reaction equation
[CH3:1][O:2][C:3]1[N:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[CH:8][CH:7]=[C:6]2O.P(Br)(Br)[Br:15].O.C([O-])([O-])=O.[Na+].[Na+]>CN(C=O)C>[Br:15][C:6]1[CH:7]=[CH:8][N:9]=[C:10]2[C:5]=1[N:4]=[C:3]([O:2][CH3:1])[CH:12]=[CH:11]2

Participants

6

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 24614Phosphorus tribromideHCID 178487891HCID 178487891, compound

Product 1

HCID 534216178-Bromo-2-methoxy-1,5-naphthyridineYield 90%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

6-(Methyloxy)-1,5-naphthyridin-4-ol (21.5 g) (for a synthesis see WO2007016610 Preparation 2 (a)) was stirred in DMF (150 ml) at 0° C. under N2, and phosphorous tribromide (13.5 ml) was added slowly. The mixture was allowed to warm to room temperature and stirred for 90 minutes. H2O (375 ml) was added and the pH was adjusted to pH 7 by addition of solid Na2CO3. The solid was isolated by filtration with suction, dried on the sinter with suction for 2 h then dried under vacuum at 45° C. to give the desired compound (26.0 g, 90%). 1H-NMR (δ, ppm, DMSO-d6): 8.59 (d, 1H), 8.30 (d, 1H), 8.08 (d, 1H), 7.33 (d, 1H), 4.06 (s, 3H).

Workup

  1. customThe solid was isolated by filtration with suction
  2. customdried on the sinter with suction for 2 h
  3. customthen dried under vacuum at 45° C.

Sources & evidence

ORD record
ord-fc8b9c330ccc4950aaa6a15f1594be02
Source dataset
uspto-grants-2012_11
Patent number
US08318940B2

Reaction notes

Loading…