Benzaldehyde → 7-Bromo-2-phenyl-[1,2,4]triazolo[1,5-a]pyridin-5-ylamine

HRID 277056

반응식

HRID 277056 반응식
[Br:1][C:2]1[CH:7]=[C:6]([NH2:8])[N:5]=[C:4]([NH2:9])[CH:3]=1.C1(C)C=C(C)C=C(C)C=1S(O[NH2:22])(=O)=O.[CH:24](=O)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.[OH-].[K+]>CO>[Br:1][C:2]1[CH:7]=[C:6]([NH2:8])[N:5]2[N:22]=[C:24]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[N:9]=[C:4]2[CH:3]=1

참가 물질

6

반응물 4

HCID 240BenzaldehydeHCID 14797Potassium HydroxideHCID 114353934-Bromo-2,6-diaminopyridineHCID 11830845O-(2,4,6-Trimethylbenzenesulfonyl)hydroxylamine

생성물 1

HCID 226296737-Bromo-2-phenyl-[1,2,4]triazolo[1,5-a]pyridin-5-ylamine수율 39.3%

시약·촉매·용매 1

HCID 887Methanol용매2회

실험 절차

To a solution of 96 mg (0.51 mmol) 4-bromo-pyridine-2,6-diamine in 2.4 ml MeOH was added 121 mg (0.56 mmol) O-mesitylenesulfonylhydroxylamine (prepared from ethyl o-mesitylene-sulfonylacetohydroxamate and HClO4 (70%)) in 0.6 ml MeOH at −5° C. and after 15min 71 mg (0.56 mmol) benzaldehyde and stirred for 30 min. The addition of 4.8 ml 1N KOH was followed by extraction with ethylacetate, drying of the organic layer with Na2SO4, and removal of the volatile components. The residue was purified by column chromatography on silica eluting with ethylacetate and hexane (2:3). 58 mg(39%) of 7-bromo-2-phenyl-[1,2,4]triazolo[1,5-a]pyridin-5-ylamine were isolated, MS m/e (%): 290 (M++2, 44).

후처리

  1. extractionwas followed by extraction with ethylacetate
  2. dry with materialdrying of the organic layer with Na2SO4, and removal of the volatile components
  3. customThe residue was purified by column chromatography on silica eluting with ethylacetate and hexane (2:3)

출처 및 근거

ORD 기록
ord-b9ea05ca0bc7405d99a5acc2a36743a9
출처 데이터셋
uspto-grants-2002_03
특허 번호
US06355653B1

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