Methanol → HCID 178522990, compound

HRID 2201541Notes

Reaction equation

HRID 2201541 reaction equation
B(Br)(Br)Br.[Br:5][C:6]1[CH:7]=[N:8][C:9]([O:23]C)=[C:10]([CH:22]=1)[C:11]([NH:13][CH2:14][C:15]1[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=1)=[O:12].CO>C(Cl)Cl>[Br:5][C:6]1[CH:7]=[N:8][C:9]([OH:23])=[C:10]([CH:22]=1)[C:11]([NH:13][CH2:14][C:15]1[CH:16]=[CH:17][C:18]([F:21])=[CH:19][CH:20]=1)=[O:12]

Participants

5

Reactant 3

HCID 887MethanolHCID 25134Boron tribromideHCID 1177715975-Bromo-N-(4-fluorobenzyl)-2-methoxynicotinamide

Product 1

HCID 178522990HCID 178522990, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

BBr3 (20 mL) was added dropwise to a mixture of compound 5-bromo-N-(4-fluorobenzyl)-2-methoxynicotinamide (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 5-bromo-N-(4-fluorobenzyl)-2-hydroxynicotinamide (1.8 g, yield: 95%). 1H-NMR (DMSO-d6, 400 MHz) δ 12.9 (s, 1H), 10.0 (t, J=4.8 Hz, 1H), 8.30 (d, J=2.8 Hz, 1H), 8.02 (s, 1H), 7.34 (dd, J=6.0, 8.8 Hz, 2H), 7.15 (d, J=8.8 Hz, 2H), 4.50 (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-785262c535e0470c91b6d65725754dfe
Source dataset
uspto-grants-2016_06
Patent number
US09364482B2

Reaction notes

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