Potassium Iodide → Ethyl 2,3-dimethyl-8-(2-ethyl-6-methylbenzylamino)-imidazo[1,2-a]pyridine-6-carboxylate

HRID 2184304Notes

Reaction equation

HRID 2184304 reaction equation
[NH2:1][C:2]1[C:3]2[N:4]([C:13]([CH3:17])=[C:14]([CH3:16])[N:15]=2)[CH:5]=[C:6]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH:7]=1.[CH2:18]([C:20]1[CH:27]=[CH:26][CH:25]=[C:24]([CH3:28])[C:21]=1[CH2:22]Cl)[CH3:19].C(=O)([O-])[O-].[Na+].[Na+].[I-].[K+]>CC(C)=O>[CH3:16][C:14]1[N:15]=[C:3]2[C:2]([NH:1][CH2:22][C:21]3[C:24]([CH3:28])=[CH:25][CH:26]=[CH:27][C:20]=3[CH2:18][CH3:19])=[CH:7][C:6]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:5][N:4]2[C:13]=1[CH3:17]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 10340Sodium CarbonateHCID 9942738Ethyl 8-amino-2,3-dimethylimidazo[1,2-a]pyridine-6-carboxylateHCID 121489182-Ethyl-6-methylbenzyl chloride

Product 1

HCID 11003040Ethyl 2,3-dimethyl-8-(2-ethyl-6-methylbenzylamino)-imidazo[1,2-a]pyridine-6-carboxylateYield 10.9%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Ethyl 8-amino-2,3-dimethylimidazo[1,2-a]pyridine-6-carboxylate (0.7 g, 3.0 mmol), 2-ethyl-6-methylbenzylchloride (0.5 g, 3.0 mmol), sodium carbonate (0.64 g, 6.0 mmol) and a catalytic amount of potassium iodide were added to acetone (50 ml) and were refluxed for 20 h. Following filtration, the acetone was evaporated under reduced pressure to give an oil. The oily product was purified by column chromatography on silica gel using diethyl ether:petroleum ether (1:1) as eluent to give 0.12 g (9%) of the title product. 1H-NMR (500 MHz, CDCl3): δ 1.25 (t, 3H), 1.5 (t, 3H), 2.35 (s, 3H), 2.42 (s, 3H), 2.44 (s, 3H), 2.75 (q, 2H), 4.45-4.5 (m, 4H), 4.9 (bs, 1H), 6.8 (s, 1H), 7.05-7.2 (m, 3H), 8.1 (s, 1H)

Workup

  1. temperaturewere refluxed for 20 h
  2. filtrationfiltration
  3. customthe acetone was evaporated under reduced pressure
  4. customto give an oil
  5. customThe oily product was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-65c306a5f6a84a2fa1e936780ab6ab8a
Source dataset
uspto-grants-2005_05
Patent number
US06900324B2

Reaction notes

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