Reaction #83787

Reaction equation

1,1'-(azodicarbonyl)dipiperidine

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

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

tributylphosphine

→

title compound

5-{4-(6-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 0.52 g of 6-chloro-2-hydroxymethyl-3-methyl-3H-imidazo[4,5-b]pyridine (prepared as described in Preparation 64), 1.23 g of 5-(4-hydroxybenzyl) -3-triphenylmethylthiazolidine-2,4-dione, 0.66 ml of tributylphosphine, 0.67 g of 1,1'-(azodicarbonyl)dipiperidine and 20 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 1:1 by volume mixture of hexane and ethyl acetate as the eluent, to give 1.51 g of the title compound, melting at 82°-84° C. (softening).

Source