p-Toluenesulfonic acid → 5-chloro-3-methyl-3H-imidazo(4,5-b)pyridine
Reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([NH:8][CH3:9])[C:5]([NH2:10])=[CH:4][CH:3]=1.[CH3:11]C1C=CC(S(O)(=O)=O)=CC=1.CC(=O)OCC>C(OC)(OC)OC>[Cl:1][C:2]1[N:7]=[C:6]2[N:8]([CH3:11])[CH:9]=[N:10][C:5]2=[CH:4][CH:3]=1Participants
5
Procedure
To a solution of 6-chloro-N2-methylpyridine-2,3-diamine (300 mg, 1.9 mmol) in HC(OMe)3 (10 mL) was added TsOH (10 mg) at 22° C. The mixture was stirred for 3 h under reflux until TLC (PE: EA=3:1) showed that the reaction was complete. The mixture was concentrated to get the crude material which was purified by using column chromatography on silica gel to give the desired product (261 mg, 81.6%) as an oil. LCMS (m/z): 168.1 [M+H]+.
Workup
- concentrationThe mixture was concentrated
- customto get the crude material which
- customwas purified
Sources & evidence
- ORD record
- ord-cedb94f8bea84501be680c7362e4dc08
- Source dataset
- uspto-grants-2016_07
- Patent number
- US09388173B2
Reaction notes
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