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

HRID 476026ノート

反応式

HRID 476026 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

  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%)

出典と根拠

ORDレコード
ord-e845220dfce3490ca1f7e02d445d7de4
出典データセット
uspto-grants-2014_01
特許番号
US08637509B2

反応ノート

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