Phosphorus oxybromide → 4-Bromo-1,5-naphthyridine

HRID 1253510Notes

Reaction equation

HRID 1253510 reaction equation
[N:1]1[C:10]2[C:5](=[N:6][CH:7]=[CH:8][CH:9]=2)[C:4](O)=[CH:3][CH:2]=1.P(Br)(Br)([Br:14])=O>>[Br:14][C:4]1[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][N:6]=2)[N:1]=[CH:2][CH:3]=1

Participants

3

Reactant 2

HCID 24613Phosphorus oxybromideHCID 178516432HCID 178516432, compound

Product 1

HCID 150257374-Bromo-1,5-naphthyridine

Conditions

Temperature
150 °C

Procedure

A flask was charged with 1,5-naphthyridin-4-ol (1 g, 6.7 mmol) and phosphorousoxybromide (5 g, 17 mmol). The mixture was heated to 150° C., stirred for 1 hour, and then cooled to room temperature. The mixture was poured into ice-water and extracted with toluene. The combined organic extracts were washed with brine, dried over sodium sulfate, filtered and concentrated to give crude product, which was re-crystallized from petroleum ether to give 4-bromo-1,5-naphthyridine.

Workup

  1. temperaturecooled to room temperature
  2. extractionextracted with toluene
  3. washThe combined organic extracts were washed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give crude product, which
  8. customwas re-crystallized from petroleum ether

Sources & evidence

ORD record
ord-221d1e0d305a498c93b370d8baa12e97
Source dataset
uspto-grants-2013_06
Patent number
US08455477B2

Reaction notes

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