Methanol → 3-Carboethoxy-2,6-dimethyl-8-(2-ethyl-6-methylbenzylamino)imidazo[1,2-a]pyridine

HRID 1386089Notes

Reaction equation

HRID 1386089 reaction equation
[NH2:1][C:2]1[C:3]2[N:4]([C:9]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[C:10]([CH3:12])[N:11]=2)[CH:5]=[C:6]([CH3:8])[CH:7]=1.[CH2:18]([C:20]1[CH:27]=[CH:26][CH:25]=[C:24]([CH3:28])[C:21]=1[CH:22]=O)[CH3:19].CO>[Cl-].[Cl-].[Zn+2].C(N(CC)CC)C>[C:13]([C:9]1[N:4]2[CH:5]=[C:6]([CH3:8])[CH:7]=[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])[C:3]2=[N:11][C:10]=1[CH3:12])([O:15][CH2:16][CH3:17])=[O:14]

Participants

6

Reactant 3

HCID 887MethanolHCID 226725728-Amino-3-carboethoxy-2,6-dimethylimidazo[1,2-a]pyridineHCID 229974692-Ethyl-6-methylbenzaldehyde

Product 1

HCID 217173483-Carboethoxy-2,6-dimethyl-8-(2-ethyl-6-methylbenzylamino)imidazo[1,2-a]pyridineYield 50.2%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalyst2×HCID 8471TriethylamineSolvent

Procedure

A mixture of 8-amino-3-carboethoxy-2,6-dimethylimidazo[1,2-a]pyridine (1.4 g, 6 mmol), 2-ethyl-6-methylbenzaldehyde (0.9 g, 6.5 mmol), ZnCl2 (1.0 g, 7.4 mmol), NaB(CN)H3 (0.41 g, 6.5 mmol) and MeOH (30 ml) was refluxed for 5 h. More ZnCl2 (0.2 g) and NaB(CN)H3 (0.1 g) were added. The reaction mixture was refluxed for additional 2 h. Triethylamin (2 ml) was added and the mixture was stirred at R.T for 10 min. The solvent was evaporated under reduced pressure and the residue was purified by column chromatography on silica gel using methylene chloride as eluent. 1.1 g (50%) of the title compound was obtained.

Workup

  1. temperaturewas refluxed for 5 h
  2. temperatureThe reaction mixture was refluxed for additional 2 h
  3. customThe solvent was evaporated under reduced pressure
  4. customthe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-f6ae35be5c554fafaaccebb4ddd260f2
Source dataset
uspto-grants-2001_07
Patent number
US06265415B1

Reaction notes

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