Methanol → 2-bromo-N-(4-fluorobenzyl)-5-hydroxyisonicotinamide

HRID 2201537Notes

Reaction equation

HRID 2201537 reaction equation
B(Br)(Br)Br.[Br:5][C:6]1[CH:7]=[C:8]([C:20]([O:23]C)=[CH:21][N:22]=1)[C:9]([NH:11][CH2:12][C:13]1[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=1)=[O:10].CO>C(Cl)Cl>[Br:5][C:6]1[CH:7]=[C:8]([C:20]([OH:23])=[CH:21][N:22]=1)[C:9]([NH:11][CH2:12][C:13]1[CH:14]=[CH:15][C:16]([F:19])=[CH:17][CH:18]=1)=[O:10]

Participants

5

Reactant 3

HCID 887MethanolHCID 25134Boron tribromideHCID 1177718312-bromo-N-(4-fluorobenzyl)-5-methoxyisonicotinamide

Product 1

HCID 1177717622-bromo-N-(4-fluorobenzyl)-5-hydroxyisonicotinamideYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

BBr3 (20 mL) was added dropwise to a mixture of 2-bromo-N-(4-fluorobenzyl)-5-methoxyisonicotinamide (2.0 g, 5.9 mmol) in DCM (10 mL) at −78° C. The mixture was stirred at RT for 10 h, and then MeOH (20 mL) was added to quench the reaction. The mixture was concentrated in vacuum to give the product of compound 2-bromo-N-(4-fluorobenzyl)-5-hydroxyisonicotinamide (1.8 g, yield: 95%). 1H-NMR (DMSO-d6, 400 MHz) δ 11.9 (s, 1H), 9.35 (s, 1H), 8.16 (s, 1H), 7.90 (s, 1H), 7.38 (t, J=6.0 Hz, 2H), 7.16 (d, J=8.8 Hz, 2H), 4.78 (s, 2H). MS (M+H)+: 325/327.

Workup

  1. customto quench
  2. customthe reaction
  3. concentrationThe mixture was concentrated in vacuum

Sources & evidence

ORD record
ord-00d6af43dc684232a482ac2ee0c10c7e
Source dataset
uspto-grants-2016_06
Patent number
US09364482B2

Reaction notes

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