HCID 22931000, compound → HCID 22931030, compound

HRID 459847Notes

Reaction equation

HRID 459847 reaction equation
C([O:8][C:9]1[CH:10]=[C:11]([C:17]2[N:22]=[C:21]([C:23]([O:25][CH3:26])=[O:24])[CH:20]=[CH:19][CH:18]=2)[CH:12]=[CH:13][C:14]=1[O:15][CH3:16])C1C=CC=CC=1>[Pd].C1COCC1.CO>[OH:8][C:9]1[CH:10]=[C:11]([C:17]2[N:22]=[C:21]([C:23]([O:25][CH3:26])=[O:24])[CH:20]=[CH:19][CH:18]=2)[CH:12]=[CH:13][C:14]=1[O:15][CH3:16]

Participants

4

Reactant 1

HCID 22931000HCID 22931000, compound

Product 1

HCID 22931030HCID 22931030, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

In a mixed solvent of THF-methanol, methyl 6-(3-benzyloxy-4-methoxyphenyl)pyridine-2-carboxylate was stirred in the presence of palladium/carbon under a hydrogen atmosphere to obtain methyl 6-(3-hydroxy-4-methoxyphenyl)pyridine-2-carboxylate. The obtained compound is reacted with cyclopropylmethyl bromide and potassium carbonate in DMF under heating to obtain methyl 6-(3-cyclopropylmethoxy-4-methoxyphenyl) pyridine-2-carboxylate, which was further reacted in a mixed solvent of THF-methanol under heating with adding a 1M aqueous sodium hydroxide solution to obtain an objective compound.

Sources & evidence

ORD record
ord-3df6202859d84f928c3cd68cdd337267
Source dataset
uspto-grants-2007_03
Patent number
US07196080B2

Reaction notes

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