Water → 6-Iodo-2-methoxy-3-[(4-methoxybenzyl)oxy]pyridine

HRID 70549

Reaction equation

[CH3:1][O-:2].[Na+].Br[C:5]1[C:10]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=2)=[CH:9][CH:8]=[C:7]([I:21])[N:6]=1.O>CS(C)=O>[I:21][C:7]1[N:6]=[C:5]([O:2][CH3:1])[C:10]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=2)=[CH:9][CH:8]=1

Participants

Conditions

Temperature: 90 °C

Procedure

Sodium methoxide (11 g) was added to a solution of 2-bromo-6-iodo-3-[(4-methoxybenzyl)oxy]pyridine (17 g) in dimethyl sulfoxide (90 mL), and the mixture was stirred at 90° C. for three hours. The reaction solution was poured into water, followed by extraction with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate and filtered. The solvent was then evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=95:5→70:30) to give 6-iodo-2-methoxy-3-[(4-methoxybenzyl)oxy]pyridine as a colorless powder (10 g, 71%).

Workup

extractionfollowed by extraction with ethyl acetate
washThe organic layer was washed with brine
dry with materialdried over anhydrous magnesium sulfate
filtrationfiltered
customThe solvent was then evaporated under reduced pressure
customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=95:5→70:30)

Sources & evidence

ORD record: ord-123f671109544a23a689988da1088225
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08822503B2

Linked notes

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