Dimethylformamide → 3-Bromo-6-methoxy-2,4-dimethylpyridine

HRID 1043889Notes

Reaction equation

[Br:1][C:2]1[C:3]([CH3:10])=[N:4][C:5](Cl)=[CH:6][C:7]=1[CH3:8].CN([CH:14]=[O:15])C.C[O-].[Na+]>O>[Br:1][C:2]1[C:3]([CH3:10])=[N:4][C:5]([O:15][CH3:14])=[CH:6][C:7]=1[CH3:8]

Participants

Conditions

Temperature: 60 °C

Procedure

3-bromo-6-chloro-2,4-dimethylpyridine obtained in Preparation Example 21 (200 mg) was added to DMF (1 mL). Sodium methoxide (28% solution in methanol, 0.741 mL) was added to the solution, and the mixture was stirred at 60° C. for 15 hours. Water was added to the reaction mixture, followed by extraction with diethyl ether. The organic layer was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/n-heptane, 0% to 10%) to give the title compound (172 mg).

Workup

extractionfollowed by extraction with diethyl ether
concentrationThe organic layer was concentrated under reduced pressure
customThe residue was purified by silica gel column chromatography (ethyl acetate/n-heptane, 0% to 10%)

Sources & evidence

ORD record: ord-9d9fa4fc783643cb9777faa0cab256b9
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08563565B2

Reaction notes

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