Reaction #83771

Reaction equation

1,1'-(azodicarbonyl)dipiperidine

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

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

tributylphosphine

→

title compound

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

Solvents

toluene

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 1.20 g of 5-chloro-2-hydroxymethyl-3-methyl-3H-imidazo[4,5-b]pyridine (prepared as described in Preparation 44), 2.83 g of 5-(4-hydroxybenzyl)-3-triphenylmethylthiazolidine-2,4-dione, 1.51 ml of tributylphosphine, 1.53 g of 1,1'-(azodicarbonyl)dipiperidine and 25 ml of toluene were used, to give the title compound as a crude product. This crude product was purified by column chromatography through silica gel, using a gradient elution method, with mixtures of hexane and ethyl acetate in ratios ranging from 2:1 to 1:1 by volume as the eluent, to give 1.29 g of the title compound, melting at 97°-99° C. (softening).

Source