Methanesulfonic Acid → 6-bromo-2-(3-methoxyphenyl)-1H-imidazo[4,5-b]pyridine
Reaction equation
O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.CS(O)(=O)=O.[NH2:20][C:21]1[C:26]([NH2:27])=[CH:25][C:24]([Br:28])=[CH:23][N:22]=1.[CH3:29][O:30][C:31]1[CH:32]=[C:33]([CH:37]=[CH:38][CH:39]=1)[C:34](O)=O.[OH-].[Na+]>>[Br:28][C:24]1[CH:25]=[C:26]2[NH:27][C:34]([C:33]3[CH:37]=[CH:38][CH:39]=[C:31]([O:30][CH3:29])[CH:32]=3)=[N:20][C:21]2=[N:22][CH:23]=1Participants
6
Conditions
- Temperature
- 100 °C
Procedure
Phosphorus pentaoxide (23.8 g) was added to methanesulfonic acid (85 ml), the mixture was stirred at 100° C. for 1 hour to give a solution. To the solution were added 2,3-diamino-5-bromopyridine (Compound of Reference Example 1) (15.8 g) and 3-methoxybenzoic acid (12.7 g), and the mixture was stirred at 100° C. for 1 hour. The reaction mixture was poured onto ice, neutralized with 8 N sodium hydroxide, and extracted with ethyl acetate-tetrahydrofuran (3:1, v/v). The organic layer was washed with water and dried over MgSO4. The solvent was distilled off under reduced pressure, and crystals were collected by filtration to obtain 6-bromo-2-(3-methoxyphenyl)-1H-imidazo[4,5-b]pyridine (21.3 g, 84%).
Workup
- customto give a solution
- stirringthe mixture was stirred at 100° C. for 1 hour
- additionThe reaction mixture was poured onto ice
- extractionextracted with ethyl acetate-tetrahydrofuran (3:1
- washThe organic layer was washed with water
- dry with materialdried over MgSO4
- distillationThe solvent was distilled off under reduced pressure, and crystals
- filtrationwere collected by filtration
Sources & evidence
- ORD record
- ord-9d0b7a4284184e4383e34f3e0041b18e
- Source dataset
- uspto-grants-2009_11
- Patent number
- US07622479B2
Reaction notes
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