Benzyl Bromide → HCID 68515317, compound

HRID 1716285Notes

Reaction equation

HRID 1716285 reaction equation
[CH2:1]([O:8][C:9](=[O:19])[NH:10][C:11]1[C:12](=[O:18])[N:13]([OH:17])[CH:14]=[CH:15][CH:16]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].[CH2:26](Br)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>CN(C=O)C.O>[CH2:1]([O:8][C:9](=[O:19])[NH:10][C:11]1[C:12](=[O:18])[N:13]([O:17][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH:14]=[CH:15][CH:16]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 68515254HCID 68515254, compound

Product 1

HCID 68515317HCID 68515317, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A suspension of (1-hydroxy-2-oxo-1,2-dihydro-pyridin-3-yl)-carbamic acid benzyl ester (1.5 g, 5.76 mmol) from Step C and K2CO3 (1.59 g, 11.5 mmol) in dry DMF (15 mL) was added benzyl bromide (0.82 mL, 6.91 mmol). The reaction mixture was stirred at room temperature for 2 h and diluted with water. The usual work-up (EtOAc extraction) and purification by chromatography (silica gel, 25% EtOAc/hexanes) gave the desired product. MS 351 (M+H)+.

Workup

  1. extractionThe usual work-up (EtOAc extraction) and purification by chromatography (silica gel, 25% EtOAc/hexanes)

Sources & evidence

ORD record
ord-4b0276dfe4304a87be5927f68f188384
Source dataset
uspto-grants-2010_09
Patent number
US07803793B2

Reaction notes

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