Reaction #50155

Reaction equation

ethyl 2-n-propyl-3-[2'-(1-trityl- 1H-tetrazol-5-yl)biphenyl-4-yl]methyl-4,5,6,7-tetrahydroimidazo[4,5-c]pyridine-4-carboxylate

potassium carbonate

ethyl bromide

dimethylformamide

→

ethyl 5-ethyl-2-n-propyl-3-[2'-(1-trityl-1H-tetrazol-5-yl)biphenyl-4-yl]methyl-4,5,6,7-tetrahydroimidazo[4,5-c]pyridine-4-carboxylate

Yield 53.9%

Solvents

ethyl acetate

Conditions

Workup

1. 1
   Washthe solution is washed with water
2. 2
   Otherdried
3. 3
   Otherevaporated
4. 4
   OtherThe residue is purified by silica gel column chromatography (solvent; chloroform/methanol)

Procedure

A mixture of ethyl 2-n-propyl-3-[2'-(1-trityl- 1H-tetrazol-5-yl)biphenyl-4-yl]methyl-4,5,6,7-tetrahydroimidazo[4,5-c]pyridine-4-carboxylate (2.00 g), potassium carbonate (1.16 g), ethyl bromide (0.61 g) and dimethylformamide (10 ml) is stirred overnight at room temperature. The mixture is diluted with ethyl acetate, and the solution is washed with water, dried and evaporated. The residue is purified by silica gel column chromatography (solvent; chloroform/methanol) to give ethyl 5-ethyl-2-n-propyl-3-[2'-(1-trityl-1H-tetrazol-5-yl)biphenyl-4-yl]methyl-4,5,6,7-tetrahydroimidazo[4,5-c]pyridine-4-carboxylate (1.12 g) as a white foam.

Source