Methyl iodide → N-((5-Bromopyridin-3-yl)methyl)-N-methylethanesulfonamide

HRID 1623508Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]([CH2:8][NH:9][S:10]([CH2:13][CH3:14])(=[O:12])=[O:11])[CH:5]=[N:6][CH:7]=1.[H-].[Na+].I[CH3:18]>CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]([CH2:8][N:9]([CH3:18])[S:10]([CH2:13][CH3:14])(=[O:11])=[O:12])[CH:5]=[N:6][CH:7]=1

Participants

Conditions

Temperature: -10 °C

Procedure

To a solution of ethanesulfonic acid (5-bromo-pyridin-3-ylmethyl)-amide (0.21 g, 0.752 mmol), prepared as described in Example 11a, in DMF (6 mL) at −10° C., was added sodium hydride (60% oil dispersion, 39 mg, 0.98 mmol). The reaction was stirred for 15 minutes at which time iodomethane (0.056 ml, 0.903 mmol) dissolved in DMF (1 mL) was added. The reaction was stirred at −10° C. for an additional 15 minutes and was then quenched with ammonia hydroxide (2 mL). The reaction was diluted with brine and extracted three times with ethyl acetate. The organic layers were combined, dried over anhydrous sodium sulfate, filtered, and concentrated. The resulting residue was purified by silica gel flash chromatography (ethyl acetate, 0 to 80%) to provide ethanesulfonic acid (5-bromo-pyridin-3-ylmethyl)-methyl-amide; MS: (ES+) m/z 293.1 (M+H)+.

Workup

additionwas added
customwas then quenched with ammonia hydroxide (2 mL)
additionThe reaction was diluted with brine
extractionextracted three times with ethyl acetate
dry with materialdried over anhydrous sodium sulfate
filtrationfiltered
concentrationconcentrated
customThe resulting residue was purified by silica gel flash chromatography (ethyl acetate, 0 to 80%)

Sources & evidence

ORD record: ord-2d4081b673b441b7af240259066e3c9e
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08778972B2

Reaction notes

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