Chlorosuccinimide → 3-Bromo-5-chloro-6-methoxy-2,4-dimethylpyridine

HRID 1043893Notes

Reaction equation

[Br:1][C:2]1[C:3]([CH3:11])=[N:4][C:5]([O:9][CH3:10])=[CH:6][C:7]=1[CH3:8].C1C(=O)N([Cl:19])C(=O)C1>CN(C=O)C>[Br:1][C:2]1[C:3]([CH3:11])=[N:4][C:5]([O:9][CH3:10])=[C:6]([Cl:19])[C:7]=1[CH3:8]

Participants

Conditions

Temperature: 80 °C

Procedure

3-bromo-6-methoxy-2,4-dimethylpyridine obtained in Preparation Example 22 (800 mg) was added to DMF (4 mL). NCS (494 mg) was added to the solution, and the mixture was stirred at 80° C. for 14 hours. The reaction mixture was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (ethyl acetate/n-heptane, 5% to 30%). The title compound (930 mg) was obtained.

Workup

concentrationThe reaction mixture was concentrated under reduced pressure
customThe resulting residue was purified by silica gel column chromatography (ethyl acetate/n-heptane, 5% to 30%)

Sources & evidence

ORD record: ord-13f780be01c64b24bea6fa44228d9c32
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08563565B2

Reaction notes

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