Benzyl Bromide → 6-(Benzyloxy)-3-bromopicolinonitrile

HRID 1479489Notes

Reaction equation

HRID 1479489 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5](=[O:8])[NH:4][C:3]=1[C:9]#[N:10].[CH2:11](Br)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>C1(C)C=CC=CC=1.C(=O)([O-])[O-].[Ag+2]>[CH2:11]([O:8][C:5]1[N:4]=[C:3]([C:9]#[N:10])[C:2]([Br:1])=[CH:7][CH:6]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 2

HCID 7498Benzyl BromideHCID 668751023-Bromo-6-oxo-1,6-dihydropyridine-2-carbonitrile

Product 1

HCID 668751786-(Benzyloxy)-3-bromopicolinonitrile

Reagents, catalysts & solvents 2

HCID 178418647HCID 178418647, compoundCatalystHCID 1140TolueneSolvent

Procedure

A solution of 3-bromo-6-oxo-1,6-dihydropyridine-2-carbonitrile (from Example 15/Step 2) (1.0 eq.), silver carbonate (1.3 eq.), and benzyl bromide (1.2 eq.) in toluene (0.16 M) was stirred in the dark at 50° C. overnight. The solvent was concentrated en vacuo, and the resulting residue was purified by a COMBIFLASH® system (ISCO) using 0-20% ethyl acetate in hexane to give 6-(benzyloxy)-3-bromopicolinonitrile.

Workup

  1. customdark at 50° C.
  2. customovernight
  3. concentrationThe solvent was concentrated en vacuo
  4. customthe resulting residue was purified by a COMBIFLASH® system (ISCO)

Sources & evidence

ORD record
ord-b1c84b26fe944b34b321951f43404622
Source dataset
uspto-grants-2016_08
Patent number
US09408907B2

Reaction notes

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