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

HRID 476026Notes

Reaction equation

HRID 476026 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, 1H), 8.07 (dd, J=8.34, 2.27 Hz, 1H), 7.92 (d, J=8.34 Hz, 1H), 5.45 (d, J=5.05 Hz, 1H), 2.76 (d, 3H).

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-e845220dfce3490ca1f7e02d445d7de4
Source dataset
uspto-grants-2014_01
Patent number
US08637509B2

Reaction notes

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