Hydrochloric Acid → N-(5-Bromopyridin-3-yl)methanesulfonamide

HRID 1695751Notes

Reaction equation

HRID 1695751 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH2:8])[CH:5]=[N:6][CH:7]=1.[CH3:9][S:10](Cl)(=[O:12])=[O:11].Cl>N1C=CC=CC=1>[Br:1][C:2]1[CH:3]=[C:4]([NH:8][S:10]([CH3:9])(=[O:12])=[O:11])[CH:5]=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 31297Methanesulfonyl chlorideHCID 8176813-Amino-5-bromopyridine

Product 1

HCID 60146007N-(5-Bromopyridin-3-yl)methanesulfonamide

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
0 °C

Procedure

5-Bromo-3-pyridinamine (200 mg) was dissolved in pyridine (5 ml), cooled to 0° C. and stirred for 10 min. Methanesulfonyl chloride (0.05 ml) was added dropwise and the reaction continued stirring for 1 hr. 2M HCl (aq) (5 ml) was added and the reaction was extracted with DCM, passed through a hydrophobic frit and evaporated to dryness. The residue was dissolved in DCM and adsorbed onto fluorosil and purified by column chromatography on silica, eluting with 50% ether/cyclohexane then 0-10% MeOH/DCM to give the title compound (96 mg).

Workup

  1. stirringthe reaction continued stirring for 1 hr
  2. extractionthe reaction was extracted with DCM
  3. customevaporated to dryness
  4. dissolutionThe residue was dissolved in DCM
  5. custompurified by column chromatography on silica
  6. washeluting with 50% ether/cyclohexane

Sources & evidence

ORD record
ord-95f5213bb702497ea1a3f41890a5dd2e
Source dataset
uspto-grants-2012_04
Patent number
US08163743B2

Reaction notes

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