3-(Difluoromethoxy)benzenesulfonyl chloride → N-(5-bromo-2-chloropyridin-3-yl)-3-(difluoromethoxy)benzenesulfonamide

HRID 2077607ノート

反応式

HRID 2077607 の反応式
[NH2:1][C:2]1[C:3]([Cl:9])=[N:4][CH:5]=[C:6]([Br:8])[CH:7]=1.[F:10][CH:11]([F:23])[O:12][C:13]1[CH:14]=[C:15]([S:19](Cl)(=[O:21])=[O:20])[CH:16]=[CH:17][CH:18]=1>N1C=CC=CC=1>[Br:8][C:6]1[CH:7]=[C:2]([NH:1][S:19]([C:15]2[CH:16]=[CH:17][CH:18]=[C:13]([O:12][CH:11]([F:10])[F:23])[CH:14]=2)(=[O:21])=[O:20])[C:3]([Cl:9])=[N:4][CH:5]=1

参加物

4

反応物 2

HCID 27782263-(Difluoromethoxy)benzenesulfonyl chlorideHCID 218583543-Amino-5-bromo-2-chloropyridine

生成物 1

HCID 57749432N-(5-bromo-2-chloropyridin-3-yl)-3-(difluoromethoxy)benzenesulfonamide収率 33.2%

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

実験手順

To a 100 mL round-bottomed flask was added 3-amino-5-bromo-2-chloropyridine (855 mg, 4122 μmol), pyridine (5 ml), 3-(difluoromethoxy)benzenesulfonyl chloride (1000 μl, 4122 μmol). The reaction mixture was stirred at room temperature for overnight (ca 16 h). The solvent was removed in vacuo and the residue was dissolved in EtOAc (50 mL), washed with water (10 mL), saturated NaCl (10 mL), dried over Na2SO4, filtered and concentrated in vacuo and the residue was purified by silica gel chromatography, eluting with 20% EtOAc/hexanes to give N-(5-bromo-2-chloropyridin-3-yl)-3-(difluoromethoxy)benzenesulfonamide (566 mg, 33% yield) as a white solid. MS (ESI pos. ion) m/z calc'd for C12H8BrClF2N2O3S: 413.9. found 414.9. 1H NMR (300 MHz, chloroform-d) δ ppm 6.53 (t, J=72.27 Hz, 1H) 6.99 (s, 1H) 7.38 (dd, J=8.18, 1.75 Hz, 1H) 7.52 (t, J=8.04 Hz, 1H) 7.58 (s, 1H) 7.62-7.68 (m, J=1.17 Hz, 1H) 8.16 (d, J=2.34 Hz, 1H) 8.21 (d, J=2.19 Hz, 1H)

後処理

  1. customThe solvent was removed in vacuo
  2. dissolutionthe residue was dissolved in EtOAc (50 mL)
  3. washwashed with water (10 mL), saturated NaCl (10 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customthe residue was purified by silica gel chromatography
  8. washeluting with 20% EtOAc/hexanes

出典と根拠

ORDレコード
ord-a60e807f8c4f47298848c8039eb01f1b
出典データセット
uspto-grants-2011_04
特許番号
US07928140B2

反応ノート

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