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

HRID 1522418Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1522418
[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

Komponenten

5

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  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%)

Quellen und Nachweise

ORD-Eintrag
ord-0a92900baa2a4b3c8b170c129dc418d2
Quelldatensatz
uspto-grants-2015_07
Patentnummer
US09073924B2

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