3-Cyanopyridine → 6-Bromo-2-(pyridin-3-YL)-[1,2,4]triazolo[1,5-A]pyridine

HRID 588419ノート

反応式

HRID 588419 の反応式
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([NH2:8])=[N:6][CH:7]=1.[C:9](#[N:16])[C:10]1[CH:15]=[CH:14][CH:13]=[N:12][CH:11]=1>[Cu]Br.O.N1C2C(=CC=C3C=2N=CC=C3)C=CC=1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([N:16]=[C:9]([C:10]3[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=3)[N:8]=2)[CH:7]=1

参加物

5

反応物 2

HCID 793-CyanopyridineHCID 706222-Amino-5-bromopyridine

生成物 1

HCID 717439846-Bromo-2-(pyridin-3-YL)-[1,2,4]triazolo[1,5-A]pyridine収率 52%

試薬・触媒・溶媒 2

HCID 212261,10-Phenanthroline hydrate触媒HCID 24593copper(I) bromide触媒

反応条件

温度
135 °C

実験手順

A mixture of 5-bromopyridin-2-amine (2 g, 11.6 mmol), nicotinonitrile (24.1 g, 231 mmol), 1,10-phenanthroline monohydrate (115 mg, 578 μmol) and copper (I) bromide (82.9 mg, 578 μmol) was placed in a 100 ml 2 necked flask and heated to 135° C. Heating was continued while air was bubbled gently through the mixture for 1.5 days. The excess nicotinonitrile was distilled off under reduced pressure and the black residue purified by chromatography (70 g silicagel column using heptane/ethyl acetate 10-100% as eluent). Final evaporation of the solvents afforded 6-bromo-2-pyridin-3-yl-[1,2,4]triazolo[1,5-a]pyridine (1.66 g, 52%) as yellow solid. Mp.: 176° C. MS: m/z=275/277 (M+H+).

後処理

  1. temperatureHeating
  2. customwas bubbled gently through the mixture for 1.5 days
  3. distillationThe excess nicotinonitrile was distilled off under reduced pressure
  4. customthe black residue purified by chromatography (70 g silicagel column using heptane/ethyl acetate 10-100% as eluent)
  5. customFinal evaporation of the solvents

出典と根拠

ORDレコード
ord-f335f1f102924476b473871767ef172d
出典データセット
uspto-grants-2016_01
特許番号
US09227970B2

反応ノート

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