Methyl iodide → N-(2-Bromo-6-methoxy-3-pyridinyl)-2-chloro-N-methyl-3-pyridinecarboxamide

HRID 53524Notes

Reaction equation

[H-].[Na+].[Br:3][C:4]1[C:9]([NH:10][C:11]([C:13]2[C:14]([Cl:19])=[N:15][CH:16]=[CH:17][CH:18]=2)=[O:12])=[CH:8][CH:7]=[C:6]([O:20][CH3:21])[N:5]=1.[CH3:22]I>CS(C)=O>[Br:3][C:4]1[C:9]([N:10]([CH3:22])[C:11]([C:13]2[C:14]([Cl:19])=[N:15][CH:16]=[CH:17][CH:18]=2)=[O:12])=[CH:8][CH:7]=[C:6]([O:20][CH3:21])[N:5]=1

Participants

Conditions

Temperature: 50 °C

Procedure

Sodium hydride (0.3 g of a 50% dispersion in mineral oil) was added to dimethylsulfoxide (10 ml) and warmed to 50° C. After cooling the mixture to room temperature, N-(2-bromo-6-methoxy-3-pyridinyl)-2-chloro-3-pyridinecarboxamide (2.0 g) was added and the resulting solution was stirred for 10 min. Methyl iodide (0.4 ml) was then added and the mixture was stirred for 30 min. The reaction mixture was quenched by the addition of water (10 ml) and ethyl acetate (100 ml) was then added. The organic phase was washed with water (4×100 ml), dried (anhydrous magnesium sulfate), concentrated, and purified on a silica gel column (methylene chloride followed by methylene chloride/ethanol, 98:2) to give 1.9 g of the title compound, suitable for use in the next reaction.

Workup

temperatureAfter cooling the mixture to room temperature
stirringthe mixture was stirred for 30 min
customThe reaction mixture was quenched by the addition of water (10 ml) and ethyl acetate (100 ml)
additionwas then added
washThe organic phase was washed with water (4×100 ml)
dry with materialdried (anhydrous magnesium sulfate)
concentrationconcentrated
custompurified on a silica gel column (methylene chloride followed by methylene chloride/ethanol, 98:2)

Sources & evidence

ORD record: ord-eb4d12397c644580a5eb2f8ae600c6ad
Source dataset: uspto-grants-1997_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05620974

Reaction notes

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