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

HRID 588419노트

반응식

HRID 588419 반응식
[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

참가 물질

5

반응물 2

HCID 793-CyanopyridineHCID 706222-Amino-5-bromopyridine

생성물 1

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

시약·촉매·용매 2

HCID 212261,10-Phenanthroline hydrate촉매HCID 24593copper(I) bromide촉매

반응 조건

온도
135 °C

실험 절차

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+).

후처리

  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

출처 및 근거

ORD 기록
ord-f335f1f102924476b473871767ef172d
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09227970B2

반응 노트

불러오는 중…