Triethylamine → N-((5-bromopyridin-3-yl)methyl)-N-(ethylsulfonyl)ethanesulfonamide

HRID 1630957Notes

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.C(N(CC)CC)C.[CH2:22]([S:24](Cl)(=[O:26])=[O:25])[CH3:23]>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]([CH2:8][N:9]([S:24]([CH2:22][CH3:23])(=[O:26])=[O:25])[S:10]([CH2:13][CH3:14])(=[O:11])=[O:12])[CH:5]=[N:6][CH:7]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of N-((5-bromopyridin-3-yl)methyl)ethanesulfonamide (1.8 g, 5.55 mmol) and triethylamine (1.683 g, 16.64 mmol) in DCM (20 mL) at 0° C. is added ethanesulfonyl chloride (1.426 g, 11.09 mmol), and the mixture is stirred at 0° C. for 1 h. Silica gel (10 g) is added and the mixture is concentrated in vacuo. The residue is purified by silica chromatography eluting with 0 to 2% MeOH-DCM to give N-((5-bromopyridin-3-yl)methyl)-N-(ethylsulfonyl)ethanesulfonamide. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.14 (t, J=7.3 Hz, 6H), 3.48 (q, J=7.3 Hz, 4H), 4.92 (s, 2H), 8.0 (t, J=2.1 Hz, 1H), 8.59 (d, J=2.0 Hz, 1H), 8.72 (d, J=2.3 Hz, 1H).

Workup

additionSilica gel (10 g) is added
concentrationthe mixture is concentrated in vacuo
customThe residue is purified by silica chromatography
washeluting with 0 to 2% MeOH-DCM

Sources & evidence

ORD record: ord-ddb6a5ec19bb444fbf132b63fd867e60
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08791141B2

Reaction notes

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