m-Anisoyl chloride → 7-Bromo-2-(3-methoxyphenyl)-[1,2,4]triazolo[1,5-a]pyridine

HRID 1802260노트

반응식

HRID 1802260 반응식
[NH2:1][N+:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][C:3]=1[NH2:9].CC1C=C(C)C=C(C)C=1S([O-])(=O)=O.[CH3:23][O:24][C:25]1[CH:26]=[C:27]([CH:31]=[CH:32][CH:33]=1)[C:28](Cl)=O>N1C=CC=CC=1>[Br:8][C:5]1[CH:6]=[CH:7][N:2]2[N:1]=[C:28]([C:27]3[CH:31]=[CH:32][CH:33]=[C:25]([O:24][CH3:23])[CH:26]=3)[N:9]=[C:3]2[CH:4]=1

참가 물질

4

반응물 2

HCID 74374m-Anisoyl chlorideHCID 866660161,2-Diamino-4-bromo-pyridinium 2,4,6-trimethyl-benzenesulfonate

생성물 1

HCID 677747487-Bromo-2-(3-methoxyphenyl)-[1,2,4]triazolo[1,5-a]pyridine

시약·촉매·용매 1

HCID 1049Pyridine용매

반응 조건

온도
85 °C

실험 절차

To a solution of 1,2-diamino-4-bromo-pyridinium-2,4,6-trimethyl-benzenesulfonate (Example 1, step a) (8 g, 20.7 mmol) in pyridine (50 ml) was added 3-methoxybenzoyl chloride (6 ml, 41.3 mmol). The reaction mixture was heated at 85° C. for 3 h. Volatiles were removed in vacuum, and the resultant residue was diluted with EtOAc (300 ml). The organic layer was washed successively with water (2×250 ml) and brine (100 ml), dried over anhydrous Na2SO4, filtered, and evaporated in vacuum. The crude material thus obtained was purified by column chromatography over silica gel (10-15% EtOAc/hexane) to afford 7-bromo-2-(3-methoxy-phenyl)-[1,2,4]triazolo[1,5-a]pyridine (8 g, quant) as white solid. LC-MS: m/z=303.8 [M+H]+.

후처리

  1. customVolatiles were removed in vacuum
  2. additionthe resultant residue was diluted with EtOAc (300 ml)
  3. washThe organic layer was washed successively with water (2×250 ml) and brine (100 ml)
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. customevaporated in vacuum
  7. customThe crude material thus obtained
  8. customwas purified by column chromatography over silica gel (10-15% EtOAc/hexane)

출처 및 근거

ORD 기록
ord-6064580fe75546e096bc2e58161eed86
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08349824B2

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