Diazomethane → Methyl 6-bromo-3-methoxypyridine-2-carboxylate

HRID 656241Notes

Reaction equation

HRID 656241 reaction equation
[N+](=[CH2:3])=[N-].[Br:4][C:5]1[N:10]=[C:9]([C:11]([O:13][CH3:14])=[O:12])[C:8]([OH:15])=[CH:7][CH:6]=1>C(OCC)C.CO>[Br:4][C:5]1[N:10]=[C:9]([C:11]([O:13][CH3:14])=[O:12])[C:8]([O:15][CH3:3])=[CH:7][CH:6]=1

Participants

5

Reactant 2

HCID 9550DiazomethaneHCID 22175135Methyl 6-bromo-3-hydroxypicolinate

Product 1

HCID 70700803Methyl 6-bromo-3-methoxypyridine-2-carboxylate

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

A solution of diazomethane in diethyl ether (about 0.4 M) is added in excess to a solution of 2.3 mmol of methyl 6-bromo-3-hydroxypyridine-2-carboxylate [321601-48-3] in 30 ml of methanol at 0° C. The mixture is stirred at 0° C. for 2 hours, then quenched with magnesium sulphate, filtered and evaporated. The crude title compound is identified by means of the Rf.

Workup

  1. customquenched with magnesium sulphate
  2. filtrationfiltered
  3. customevaporated

Sources & evidence

ORD record
ord-1ca5ff9f07c24d21bca5e246b7fb6232
Source dataset
uspto-grants-2011_12
Patent number
US08071651B2

Reaction notes

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