N-bromobutanimide → HCID 86644895, 화합물

HRID 1874919노트

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HRID 1874919 반응식
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]#[N:9])[CH:5]=[C:4]([O:10][C:11]2[C:16]([Cl:17])=[CH:15][CH:14]=[C:13]([CH3:18])[C:12]=2[F:19])[N:3]=1.C1C(=O)N([Br:27])C(=O)C1>C(Cl)(Cl)(Cl)Cl.CC(N=NC(C#N)(C)C)(C#N)C>[Br:27][CH2:18][C:13]1[C:12]([F:19])=[C:11]([O:10][C:4]2[CH:5]=[C:6]([C:8]#[N:9])[CH:7]=[C:2]([Cl:1])[N:3]=2)[C:16]([Cl:17])=[CH:15][CH:14]=1

참가 물질

5

반응물 2

HCID 67184N-bromobutanimideHCID 866448942-Chloro-6-[(6-chloro-2-fluoro-3-methylphenyl)oxy]-4-pyridinecarbonitrile

생성물 1

HCID 86644895HCID 86644895, 화합물수율 57.2%

시약·촉매·용매 2

HCID 6547Azobisisobutyronitrile촉매HCID 5943Carbon Tetrachloride용매

실험 절차

2-chloro-6-[(6-chloro-2-fluoro-3-methylphenyl)oxy]-4-pyridinecarbonitrile (3.65 g, 12.28 mmol) and NBS (2.187 g, 12.28 mmol) were combined in carbon tetrachloride (100 mL) with a catalytic amount of AIBN (0.101 g, 0.614 mmol) and stirred at reflux for 16 h. The reaction mixture was washed with water, dried over MgSO4, filtered and concentrated to dryness. The residue was purified by chromatography on 120 g silica gel eluted with 0% to 10% Et2O in hexanes to give the desired product, 2-{[3-(bromomethyl)-6-chloro-2-fluorophenyl]oxy}-6-chloro-4-pyridinecarbonitrile (2.64 g, 7.02 mmol, 57.2% yield), as a white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm (8.01 (s, 1H), 7.96 (s, 1H), 7.50-7.62 (m, 2H), 4.75 (s, 2H). LC-MS (ES+) m/z 374.98, 377.01, 379.03 [M+H].

후처리

  1. temperatureat reflux for 16 h
  2. washThe reaction mixture was washed with water
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated to dryness
  6. customThe residue was purified by chromatography on 120 g silica gel
  7. washeluted with 0% to 10% Et2O in hexanes

출처 및 근거

ORD 기록
ord-c47caaf6356f425794ab8e771e5bbf48
출처 데이터셋
uspto-grants-2012_11
특허 번호
US08304419B2

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