Nitrilooxonium tetrafluoroborate → 5-Bromo-3-fluoropyridine-2-carboxamide

HRID 873316Notes

Reaction equation

HRID 873316 reaction equation
[F:1][B-](F)(F)F.N#[O+].N[C:9]1[C:10]([C:16]([NH2:18])=[O:17])=[N:11][CH:12]=[C:13]([Br:15])[CH:14]=1>C(Cl)Cl>[F:1][C:9]1[C:10]([C:16]([NH2:18])=[O:17])=[N:11][CH:12]=[C:13]([Br:15])[CH:14]=1

Participants

4

Reactant 2

HCID 11137142Nitrilooxonium tetrafluoroborateHCID 210758623-Amino-5-bromopyridine-2-carboxamide

Product 1

HCID 210758715-Bromo-3-fluoropyridine-2-carboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Nitrosonium tetrafluoroborate (300 mg, 2.58 mmol) was added to a suspension of 3-amino-5-bromopyridine-2-carboxamide (466 mg, 2.15 mmol) in DCM (30 mL) and the mixture stirred at room temperature for 16 h. The solvent was removed in vacuo and toluene (30 mL) was added and the mixture heated to reflux for 2 h. After cooling to room temperature the solvent was removed in vacuo and the crude slurried in DCM (10 mL), filtered, washed with DCM and dried in vacuo at 40° C. to give 3-fluoro-5-bromopyridine-2-carboxamide which was used directly without further purification.

Workup

  1. customThe solvent was removed in vacuo and toluene (30 mL)
  2. additionwas added
  3. temperaturethe mixture heated
  4. temperatureto reflux for 2 h
  5. temperatureAfter cooling to room temperature the solvent
  6. customwas removed in vacuo
  7. filtrationfiltered
  8. washwashed with DCM
  9. customdried in vacuo at 40° C.

Sources & evidence

ORD record
ord-bf8a7275261a4c4287ba30dc646f7e18
Source dataset
uspto-grants-2015_03
Patent number
US08975406B2

Reaction notes

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