2-Bromopyridine → Pyridine sulfonamide

HRID 1186436Notes

Reaction equation

HRID 1186436 reaction equation
BrC1C=CC=C[N:3]=1.C([Li])CCC.S(Cl)(Cl)(=O)=O.[N:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[S:24]([NH2:27])(=[O:26])=[O:25]>CCCCCC.CO.C(OCC)C>[NH3:3].[N:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[S:24]([NH2:27])(=[O:26])=[O:25]

Participants

9

Reactant 4

HCID 79732-BromopyridineHCID 24648Sulfuryl chlorideHCID 12000791Pyridine sulfonamideHCID 178418339Butyllithium

Product 2

HCID 222AmmoniaHCID 12000791Pyridine sulfonamideYield 15%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 3283Diethyl EtherSolventHCID 8058HexaneSolvent

Procedure

According to Reference Example 9-8, by use of 2-bromopyridine (500 mg, 3.2 mmol), diethyl ether (5 mL), n-butyllithium (a 1.56 mol/L solution in hexane, 2.5 mL, 3.8 mmol), sulfuryl chloride (0.28 mL, 3.5 mmol) and a 7 mol/L solution of ammonia in methanol (2 mL), pyridine-2-sulfonamide (Compound FI) (77 mg, yield: 15%) was obtained.

Sources & evidence

ORD record
ord-fc8ae1c0e7fc4baea94560276d2966ad
Source dataset
uspto-grants-2014_03
Patent number
US08673908B2

Reaction notes

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