m-Anisoyl chloride → 7-Bromo-2-(3-methoxyphenyl)-[1,2,4]triazolo[1,5-a]pyridine
Reaction equation
[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]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 85 °C
Procedure
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]+.
Workup
- customVolatiles were removed in vacuum
- additionthe resultant residue was diluted with EtOAc (300 ml)
- washThe organic layer was washed successively with water (2×250 ml) and brine (100 ml)
- dry with materialdried over anhydrous Na2SO4
- filtrationfiltered
- customevaporated in vacuum
- customThe crude material thus obtained
- customwas purified by column chromatography over silica gel (10-15% EtOAc/hexane)
Sources & evidence
- ORD record
- ord-6064580fe75546e096bc2e58161eed86
- Source dataset
- uspto-grants-2013_01
- Patent number
- US08349824B2
Reaction notes
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