Methanesulfonic Acid → 5-phenyl-2-(3-methoxyphenyl)-1H-imidazo[4,5-b]pyridine
Reaction equation
P(Cl)(Cl)(Cl)(Cl)Cl.CS(O)(=O)=O.[NH2:12][C:13]1[C:18]([NH2:19])=[CH:17][CH:16]=[C:15]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[N:14]=1.[CH3:26][O:27][C:28]1[CH:29]=[C:30]([CH:34]=[CH:35][CH:36]=1)[C:31](O)=O.[OH-].[Na+]>>[C:20]1([C:15]2[N:14]=[C:13]3[N:12]=[C:31]([C:30]4[CH:34]=[CH:35][CH:36]=[C:28]([O:27][CH3:26])[CH:29]=4)[NH:19][C:18]3=[CH:17][CH:16]=2)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1Participants
6
Conditions
- Temperature
- 120 °C
Procedure
Phosphorus pentachloride (0.5 g) was added to methanesulfonic acid (2 ml), and the mixture was stirred at 120° C. for 1 hour to make a solution. To the solution were added 2,3-diamino-6-phenylpyridine (Compound of Reference Example 113) (0.2 g) and 3-methoxybenzoic acid (0.17 g), and the mixture was stirred at 120° C. for 1 hour. The reaction mixture was poured onto ice, neutralized with 8 N sodium hydroxide solution 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 the resulting crystals were collected by filtration to obtain 5-phenyl-2-(3-methoxyphenyl)-1H-imidazo[4,5-b]pyridine (0.18 g, 55%).
Workup
- stirringthe mixture was stirred at 120° 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
- filtrationthe resulting crystals were collected by filtration
Sources & evidence
- ORD record
- ord-869163343dec442e8c6b99a35170a94d
- Source dataset
- uspto-grants-2009_11
- Patent number
- US07622479B2
Reaction notes
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