Sodium Carbonate → Methyl 6-(3,4-dimethoxyphenyl)pyridine-2-carboxylate

HRID 459840Notes

Reaction equation

HRID 459840 reaction equation
Cl[C:2]1[N:7]=[C:6]([C:8]([O:10][CH3:11])=[O:9])[CH:5]=[CH:4][CH:3]=1.[CH3:12][O:13][C:14]1[CH:15]=[C:16](OB(O)O)[CH:17]=[CH:18][C:19]=1[O:20][CH3:21].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O.C(COC)OC>[CH3:12][O:13][C:14]1[CH:15]=[C:16]([C:2]2[N:7]=[C:6]([C:8]([O:10][CH3:11])=[O:9])[CH:5]=[CH:4][CH:3]=2)[CH:17]=[CH:18][C:19]=1[O:20][CH3:21]

Participants

8

Reactant 4

HCID 10340Sodium CarbonateHCID 11776TriphenylphosphineHCID 242723Methyl 6-chloropicolinateHCID 226370253,4-Dimethoxyphenylboric acid

Product 1

HCID 22931007Methyl 6-(3,4-dimethoxyphenyl)pyridine-2-carboxylate

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

To a mixture of methyl 6-chloropyridine-2-carboxylate, 3,4-dimethoxyphenylboric acid, dimethoxyethane and water were added palladium acetate, triphenylphosphine and sodium carbonate, and they were reacted at 100° C. for 1 hour to obtain methyl 6-(3,4-dimethoxyphenyl)pyridine-2-carboxylate. Thus obtained compound was reacted at 60° C. for 30 minutes in a mixed solution of THF-methanol with adding a 1M aqueous sodium hydroxide solution, whereby 6-(3,4-dimethoxyphenyl)pyridine-2-carboxylic acid was obtained.

Workup

  1. customwere reacted at 100° C. for 1 hour

Sources & evidence

ORD record
ord-6cbef78d42a84cd385ab04c16eddb6af
Source dataset
uspto-grants-2007_03
Patent number
US07196080B2

Reaction notes

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