Pyridine → 5-Bromo-N-methyl-2-pyridinesulfonamide

HRID 1522418Notes

Reaction equation

HRID 1522418 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([S:8](Cl)(=[O:10])=[O:9])=[N:6][CH:7]=1.[N:12]1C=CC=C[CH:13]=1.CN>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([NH:12][CH3:13])(=[O:10])=[O:9])=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 6329MethylamineHCID 445580975-Bromopyridine-2-sulfonyl chloride

Product 1

HCID 584364765-Bromo-N-methyl-2-pyridinesulfonamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5-Bromo-2-pyridinesulfonyl chloride (500 mg, 1.949 mmol) was added to a 0° C. solution of pyridine (0.315 ml, 3.90 mmol), methylamine (0.975 ml, 1.949 mmol, 2M in THF) and CH2Cl2 (2 mL). The reaction mixture was stirred at room temperature for 1 hr, then quenched with brine. The contents were extracted with DCM, dried, filtered, and concentrated in vacuo. The crude product was purified by silica gel chromatography (eluent: 50%, EtOAC/CH2Cl2). The product was collected as a clear oil, 225 mg (75%). LCMS E-S (M+H)=251.1. 1H NMR (400 MHz, Chloroform-d) δ ppm 8.77 (s, 1 H), 8.07 (dd, J=8.34, 2.27 Hz, 1 H), 7.92 (d, J=8.34 Hz, 1 H), 5.45 (d, J=5.05 Hz, 1 H), 2.76 (d, 3 H).

Workup

  1. customquenched with brine
  2. extractionThe contents were extracted with DCM
  3. customdried
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified by silica gel chromatography (eluent: 50%, EtOAC/CH2Cl2)
  7. customThe product was collected as a clear oil, 225 mg (75%)

Sources & evidence

ORD record
ord-0a92900baa2a4b3c8b170c129dc418d2
Source dataset
uspto-grants-2015_07
Patent number
US09073924B2

Reaction notes

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