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

HRID 2401493ノート

反応式

HRID 2401493 の反応式
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

参加物

7

反応物 4

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

生成物 1

HCID 578393623-(Pyridin-3-yloxy)benzonitrile収率 76.5%

試薬・触媒・溶媒 2

HCID 164827Copper oxide (CuO)触媒HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-d9e7aca06b82472db974ec17d79f9c99
出典データセット
uspto-grants-2014_08
特許番号
US08796295B2

反応ノート

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