Pyridine → 3-(Pyridin-3-yloxy)benzonitrile

HRID 2401493

반응식

HRID 2401493 반응식
Br[C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[C:5]#[N:6].[OH:10][C:11]1[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=1.C([O-])([O-])=O.[K+].[K+].N1C=CC=CC=1>[O-2].[Cu+2].C(Cl)Cl>[N:13]1[CH:14]=[CH:15][CH:16]=[C:11]([O:10][C:2]2[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=2)[C:5]#[N:6])[CH:12]=1

참가 물질

7

반응물 4

HCID 1049PyridineHCID 79713-HydroxypyridineHCID 11430Potassium CarbonateHCID 233813-Bromobenzonitrile

생성물 1

HCID 578393623-(Pyridin-3-yloxy)benzonitrile수율 76.5%

시약·촉매·용매 2

HCID 164827Copper oxide (CuO)촉매HCID 6344Dichloromethane용매

실험 절차

Cu(II) oxide (2.1 g, 26 mmol, 2.5 eq) was added to a mixture of 3-bromobenzonitrile (3.8 g, 21 mmol, 2.0 eq), 3-hydroxypyridine (1.0 g, 10 mmol, 1.0 eq), K2CO3 (3.0 g, 22 mmol, 2.1 eq) and pyridine (35 mL) at 80° C. The mixture was refluxed vigorously for 20 h and cooled to rt. CH2Cl2 was added and the mixture was filtered through celite. Pyridine was removed in vacuo and the residue dissolved in EtOAc and washed with 1N HCl (1×), 1N NaOH (1×), brine (1×), dried (MgSO4), filtered and concentrated in vacuo. Purification by flash chromatography on silica gel afforded 1.5 g (73%) of the title compound as a white solid: 1H NMR (400 MHz, DMSO-d6) δ 8.15 (dd, J=4.9, 1.6 Hz, 1H), 7.89 (td, J=7.6, 2.0 Hz, 1H), 7.69-7.67 (m, 2H), 7.61 (t, J=8.0 Hz, 1H), 7.51-7.49 (m, 1H), 7.17 (dd, J=7.0, 5.1 Hz, 1H), 7.12 (d, J=8.3 Hz, 1H); ES-MS [M+1]+: 197.2.

후처리

  1. temperatureThe mixture was refluxed vigorously for 20 h
  2. filtrationthe mixture was filtered through celite
  3. customPyridine was removed in vacuo
  4. dissolutionthe residue dissolved in EtOAc
  5. washwashed with 1N HCl (1×), 1N NaOH (1×), brine (1×)
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customPurification by flash chromatography on silica gel

출처 및 근거

ORD 기록
ord-d9e7aca06b82472db974ec17d79f9c99
출처 데이터셋
uspto-grants-2014_08
특허 번호
US08796295B2

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