p-Toluenesulfonic acid → 5-chloro-3-methyl-3H-imidazo(4,5-b)pyridine

HRID 1399867Notes

Reaction equation

HRID 1399867 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]=1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 8857Ethyl AcetateHCID 249039426-Chloro-N2-methylpyridine-2,3-diamine

Product 1

HCID 127823875-chloro-3-methyl-3H-imidazo(4,5-b)pyridineYield 2,681.7%

Reagents, catalysts & solvents 1

HCID 9005Trimethyl orthoformateSolvent

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

  1. concentrationThe mixture was concentrated
  2. customto get the crude material which
  3. customwas purified

Sources & evidence

ORD record
ord-c477d8fbe3ff43a598267d69addd9666
Source dataset
uspto-grants-2014_12
Patent number
US08906900B2

Reaction notes

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