Hydrochloric Acid → N-(5-Bromo-2-methoxypyridin-3-yl)cyclopropanesulfonamide

HRID 1695732Notes

Reaction equation

HRID 1695732 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH2:10])[C:5]([O:8][CH3:9])=[N:6][CH:7]=1.[CH:11]1([S:14](Cl)(=[O:16])=[O:15])[CH2:13][CH2:12]1.Cl>N1C=CC=CC=1>[Br:1][C:2]1[CH:3]=[C:4]([NH:10][S:14]([CH:11]2[CH2:13][CH2:12]2)(=[O:16])=[O:15])[C:5]([O:8][CH3:9])=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 2760919Cyclopropanesulfonyl chlorideHCID 447548695-Bromo-2-methoxypyridin-3-amine

Product 1

HCID 57843318N-(5-Bromo-2-methoxypyridin-3-yl)cyclopropanesulfonamideYield 93.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

5-Bromo-2-(methyloxy)-3-pyridinamine (1.05 g, 5.17 mmol, available from Asymchem) was dissolved in pyridine (10 ml) and cyclopropanesulfonyl chloride (1.818 g, 12.93 mmol) was added dropwise. The reaction mixture was stirred at room temperature overnight, then acidified to ca. pH 2 with 2M HCl (aq) and extracted into DCM. The DCM was passed through a hydrophobic frit and the filtrate was evaporated to dryness to afford the title compound (1.48 g).

Workup

  1. extractionextracted into DCM
  2. customthe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-923c2ce2daab4032b1730acf2df5b17c
Source dataset
uspto-grants-2012_04
Patent number
US08163743B2

Reaction notes

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