Phosphorus oxybromide → HCID 86687559, compound

HRID 1473504Notes

Reaction equation

HRID 1473504 reaction equation
[CH2:1]([S:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13](O)=[CH:14][CH:15]=[N:16]2)=[CH:11][N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.P(Br)(Br)([Br:22])=O>C(#N)C>[CH2:1]([S:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13]([Br:22])=[CH:14][CH:15]=[N:16]2)=[CH:11][N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 24613Phosphorus oxybromideHCID 178516457HCID 178516457, compound

Product 1

HCID 86687559HCID 86687559, compoundYield 73.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
65 °C

Procedure

To a flask fitted with a reflux condenser was added 7-(benzylthio)-1,6-naphthyridin-4-ol (0.160 g, 0.596 mmol) followed by acetonitrile (2 mL) and phosphorous oxybromide (0.121 mL, 1.193 mmol). The reaction was heated to 65° C. for 1 hour. The reaction was cooled to room temperature and quenched with aqueous sodium bicarbonate (20 mL) and was washed with DCM (20 mL×3). The organic layers were combined, dried over magnesium sulfate, filtered and concentrated. The resulting material was purified via silica gel MPLC (40 g), eluting with 0% to 100% ethyl acetate in heptanes. The fractions were collected and the solvent was removed under reduced pressure to provide 0.145 g of 7-(benzylthio)-4-bromo-1,6-naphthyridine as a yellow solid. m/z (ESI) 333.0 (M+H)+.

Workup

  1. customTo a flask fitted with a reflux condenser
  2. temperatureThe reaction was cooled to room temperature
  3. customquenched with aqueous sodium bicarbonate (20 mL)
  4. washwas washed with DCM (20 mL×3)
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe resulting material was purified via silica gel MPLC (40 g)
  9. washeluting with 0% to 100% ethyl acetate in heptanes
  10. customThe fractions were collected
  11. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-12beb3443803462596d7596d101422e7
Source dataset
uspto-grants-2015_04
Patent number
US09012443B2

Reaction notes

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