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

HRID 1522418노트

반응식

HRID 1522418 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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).

후처리

  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%)

출처 및 근거

ORD 기록
ord-0a92900baa2a4b3c8b170c129dc418d2
출처 데이터셋
uspto-grants-2015_07
특허 번호
US09073924B2

반응 노트

불러오는 중…