Trimethylsilyldiazomethane → HCID 70664073, compound

HRID 2036790Notes

Reaction equation

HRID 2036790 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([S:9]([NH2:12])(=[O:11])=[O:10])[C:5]([OH:8])=[N:6][CH:7]=1.[CH3:13][Si](C=[N+]=[N-])(C)C>CO.C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]([S:9]([NH2:12])(=[O:11])=[O:10])[C:5](=[O:8])[N:6]([CH3:13])[CH:7]=1.[Br:1][C:2]1[CH:3]=[C:4]([S:9]([NH2:12])(=[O:11])=[O:10])[C:5]([O:8][CH3:13])=[N:6][CH:7]=1

Participants

5

Reactant 2

HCID 167693TrimethylsilyldiazomethaneHCID 178514683HCID 178514683, compound

Product 2

HCID 67055872HCID 67055872, compoundYield 34%HCID 70664073HCID 70664073, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

To a solution of 5-bromo-2-hydroxypyridine-3-sulfonamide (0.5 g, 1.9 mmol) in MeOH/DCM (15 mL, 1:1) at −10° C. was added trimethylsilyldiazomethane solution (2 M, 1.97 mL, 3.9 mmol). Upon completion of addition, the reaction mixture was concentrated and the resulting residue was purified by column chromatography using methanol and CHCl3 to 5-bromo-1-methyl-2-oxo-1,2-dihydropyridine-3-sulfonamide yield 5-bromo-1-methyl-2-oxo-1,2-dihydropyridine-3-sulfonamide (280 mg, 53% yield) and 5-bromo-2-methoxypyridine-3-sulfonamide (180 mg, 34% yield). Data for 5-bromo-1-methyl-2-oxo-1,2-dihydropyridine-3-sulfonamide: 1H NMR (400 MHz, DMSO-d6, δ): 8.42 (d, 1H, J=2.8 Hz); 7.99 (d, 1H, J=2.8 Hz); 7.14 (s, 1H); 3.52 (s, 3H). Data for 5-bromo-2-methoxypyridine-3-sulfonamide: 1H NMR (400 MHz, DMSO-d6, δ): 8.54 (d, 1H, J=2.4 Hz); 8.17 (d, 1H, J=2.4 Hz); 7.51 (s, 1H); 4.00 (s, 3H).

Workup

  1. additionUpon completion of addition
  2. concentrationthe reaction mixture was concentrated
  3. customthe resulting residue was purified by column chromatography

Sources & evidence

ORD record
ord-8faef6533b104dbca8bfc4434a83fd4f
Source dataset
uspto-grants-2013_11
Patent number
US08575184B2

Reaction notes

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