Hydrogen Bromide → 4-Bromothieno[3,2-C]pyridin-6-amine
Reaction equation
[C:1]([CH2:3][C:4]1[S:5][CH:6]=[CH:7][C:8]=1[C:9]#[N:10])#[N:2].[BrH:11].[OH-].[Na+]>C(O)(=O)C>[NH2:2][C:1]1[N:10]=[C:9]([Br:11])[C:8]2[CH:7]=[CH:6][S:5][C:4]=2[CH:3]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
2-Cyanomethyl-3-cyanothiophene (823 mg) was added to a solution (30 ml) of 25% hydrogen bromide in acetic acid, and the resulting mixture was stirred under ice-cooling for 90 min, which was neutralized with a 8N-aqueous solution of sodium hydroxide and then extracted with ethyl acetate. The organic layer was washed with water, dried (over MgSO4) and evaporated. The residue was purified by silica gel column chromatography (ethyl acetate/hexane system), to give the title compound as a yellow solid (894 mg, yield; 70%).
Workup
- temperaturecooling for 90 min
- extractionextracted with ethyl acetate
- washThe organic layer was washed with water
- dry with materialdried (over MgSO4)
- customevaporated
- customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane system)
Sources & evidence
- ORD record
- ord-ed43612da5b14cde9caf1b664ee6cd6d
- Source dataset
- uspto-grants-2004_09
- Patent number
- US06790844B2
Reaction notes
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