Reaction #83763

Reaction equation

1,1'-(azodicarbonyl)dipiperidine

3-ethyl-2-hydroxymethyl-3H-imidazo[4,5-b]pyridine

5-(4-hydroxybenzyl)-3-triphenylmethylthiazolidine-2,4-dione

tributylphosphine

→

title compound

5-{4-(3-Ethyl-3H-imidazo[4,5-b]pyridin-2-ylmethoxy)-benzyl}3-triphenylmethylthiazolidine-2,4-dione

Solvents

benzene

Conditions

Workup

1. 1
   OtherA procedure similar to that described in Preparation 4

Procedure

A procedure similar to that described in Preparation 4 was repeated, except that 0.5 g of 3-ethyl-2-hydroxymethyl-3H-imidazo[4,5-b]pyridine (prepared as described in Preparation 28), 1.313 g of 5-(4-hydroxybenzyl)-3-triphenylmethylthiazolidine-2,4-dione, 0.77 ml of tributylphosphine, 0.712 g of 1,1'-(azodicarbonyl)dipiperidine and 80 ml of benzene were used, to give the title compound as a crude product. This crude product was purified by column chromatography through silica gel, using a 1:3 by volume mixture of hexane and ethyl acetate as the eluent, to give 300 mg of the title compound having Rf=0.55 (on silica gel thin layer chromatography using a 1:3 by volume mixture of hexane and ethyl acetate as the developing solvent).

Source