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

HRID 1374166Notes

Reaction equation

HRID 1374166 reaction equation
N[C:2]1[C:3]([C:9]([NH2:11])=[O:10])=[N:4][CH:5]=[C:6]([Br:8])[CH:7]=1.[F:12][B-](F)(F)F.N#[O+]>C(Cl)Cl>[Br:8][C:6]1[CH:7]=[C:2]([F:12])[C:3]([C:9]([NH2:11])=[O:10])=[N:4][CH:5]=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

To a solution of 3-amino-5-bromopyridine-2-carboxamide (40.0 g, 185.2 mmol) in CH2Cl2 was added nitrosonium tetrafluoroborate (22.71 g, 191.4 mmol). The reaction was stirred at room temperature for 4.5 hours, then concentrated in vacuo and azeotroped with toluene. The residue was suspended in toluene (1100 mL) and heated to 100° C. for 2 hours. The reaction was concentrated in vacuo, and the residue suspended in CH2Cl2. The solid was collected to provide 5-bromo-3-fluoropyridine-2-carboxamide that gave proton NMR spectra consistent with theory and a mass ion (ES+) of 219.1 for M+H+(79Br).

Workup

  1. concentrationconcentrated in vacuo
  2. customazeotroped with toluene
  3. temperatureheated to 100° C. for 2 hours
  4. concentrationThe reaction was concentrated in vacuo
  5. customThe solid was collected

Sources & evidence

ORD record
ord-130ba909dbc743a8b132ae93555e18d3
Source dataset
uspto-grants-2007_01
Patent number
US07163951B2

Reaction notes

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