Oxonium, trimethyl-, tetrafluoroborate(1-) (1:1) → HCID 86728275, compound

HRID 1776879Notes

Reaction equation

HRID 1776879 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][C:5]([O:11][CH3:12])=[C:6]([CH:10]=1)[C:7]([NH2:9])=[O:8].F[B-](F)(F)F.[CH3:18][O+](C)C>ClCCl>[Br:1][C:2]1[CH:3]=[N:4][C:5]([O:11][CH3:12])=[C:6]([CH:10]=1)[C:7](=[NH:9])[O:8][CH3:18]

Participants

4

Reactant 2

HCID 2735153Oxonium, trimethyl-, tetrafluoroborate(1-) (1:1)HCID 702817185-Bromo-2-methoxypyridine-3-carboxamide

Product 1

HCID 86728275HCID 86728275, compoundYield 124.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-bromo-2-methoxynicotinamide (4.7 g, 0.02 mol) in dichloromethane (100 mL) was added Trimethyl-oxonium tetrafluoro borate (4.6 g, 0.02 mol) at room temperature. The mixture was stirred at room for 12 hours. The solvent was moved off and the resulting residue was washed with dichloromethane (50 mL*2), then dry to provide methyl 5-bromo-2-methoxynicotinimidate (6.1 g, yield 91%). 1HNMR (400 MHz, D2O) δ 8.46 (m, 2H), 4.22 (s, 3H), 4.02 (s, 3H), 1.93 (s, 2H). MS (M+H)+: 333/335.

Workup

  1. washthe resulting residue was washed with dichloromethane (50 mL*2)
  2. customdry

Sources & evidence

ORD record
ord-f46a938fa930403bbcef6de9ede254a4
Source dataset
uspto-grants-2016_02
Patent number
US09265773B2

Reaction notes

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