Nitrilooxonium tetrafluoroborate → 4-Bromo-6-methoxy-[1,5]naphthyridine-3-diazonium tetrafluoroborate

HRID 1441248Notes

Reaction equation

HRID 1441248 reaction equation
[Br:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:12][CH3:13])[N:10]=2)[N:5]=[CH:4][C:3]=1[NH2:14].[F:15][B-:16]([F:19])([F:18])[F:17].[N:20]#[O+]>C1COCC1>[F:15][B-:16]([F:19])([F:18])[F:17].[Br:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:12][CH3:13])[N:10]=2)[N:5]=[CH:4][C:3]=1[N+:14]#[N:20]

Participants

4

Reactant 2

HCID 11137142Nitrilooxonium tetrafluoroborateHCID 684539634-Bromo-6-methoxy-1,5-naphthyridin-3-amine

Product 1

HCID 866135404-Bromo-6-methoxy-[1,5]naphthyridine-3-diazonium tetrafluoroborateYield 90%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4-bromo-6-methoxy-[1,5]naphthyridin-3-ylamine (25.2 g, 99.2 mmole) in dry THF (400 mL) was maintained at −5° C. while nitrosonium tetrafluoroborate (12.9 g, 110 mmole) was added portionwise over 30 min (approximately 2 g portions). The reaction was continued for an additional 1 hr at −5° C., at which time TLC* and LC/MS indicated that the reaction was complete. The orange solid was collected by suction filtration, washed with ice-cold THF and dried under vacuum to provide the title compound (31.42 g, 90%).

Workup

  1. additionwas added portionwise over 30 min (approximately 2 g portions)
  2. filtrationThe orange solid was collected by suction filtration
  3. washwashed with ice-cold THF
  4. customdried under vacuum

Sources & evidence

ORD record
ord-ffcc03b222bb4a7ab439486d040b78dd
Source dataset
uspto-grants-2010_02
Patent number
US07655648B2

Reaction notes

Loading…