Water → 6-Methoxy-5-phenylpyridine-2-carbaldehyde

HRID 70514Notes

Reaction equation

[C:1]1(B(O)O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(=O)([O-])[O-].[Na+].[Na+].Br[C:17]1[CH:18]=[CH:19][C:20]([CH:25]=[O:26])=[N:21][C:22]=1[O:23][CH3:24].O>COCCOC>[CH3:24][O:23][C:22]1[N:21]=[C:20]([CH:25]=[O:26])[CH:19]=[CH:18][C:17]=1[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

Conditions

Temperature: 80 °C

Procedure

Tetrakistriphenylphosphine palladium (403 mg), phenylboronic acid (510 mg) and a 2 M sodium carbonate solution (3.5 mL) were sequentially added to a solution of 5-bromo-6-methoxypyridine-2-carbaldehyde (753 mg) in 1,2-dimethoxyethane (23 mL) in a nitrogen atmosphere, and the mixture was stirred at 80° C. for three hours. Water was added to the reaction solution at room temperature, followed by extraction with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate and filtered. The solvent was then evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=50:1→1:1) and further purified by silica gel column chromatography (hexane:ethyl acetate=50:1) to give 6-methoxy-5-phenylpyridine-2-carbaldehyde (445 mg, 60%).

Workup

extractionfollowed by extraction with ethyl acetate
washThe organic layer was washed with brine
dry with materialdried over anhydrous sodium sulfate
filtrationfiltered
customThe solvent was then evaporated under reduced pressure
customThe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=50:1→1:1)
customfurther purified by silica gel column chromatography (hexane:ethyl acetate=50:1)

Sources & evidence

ORD record: ord-30ba5ac72c6049e8bc03ef55a1b59eac
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08822503B2

Reaction notes

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