Tributylphosphine → 5-{4-(5-Ethoxy-3-methylimidazo[5,4-b]pyridin-2-ylmethoxy)benzyl}-3-triphenylmethylthiazolidine-2,4-dione

HRID 1601868Notes

Reaction equation

HRID 1601868 reaction equation
[CH2:1]([O:3][C:4]1[N:9]=[C:8]2[N:10]([CH3:15])[C:11]([CH2:13][OH:14])=[N:12][C:7]2=[CH:6][CH:5]=1)[CH3:2].O[C:17]1[CH:49]=[CH:48][C:20]([CH2:21][CH:22]2[S:26][C:25](=[O:27])[N:24]([C:28]([C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=3)([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)[C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[C:23]2=[O:47])=[CH:19][CH:18]=1.C(P(CCCC)CCCC)CCC.N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O>C1(C)C=CC=CC=1>[CH2:1]([O:3][C:4]1[N:9]=[C:8]2[N:10]([CH3:15])[C:11]([CH2:13][O:14][C:17]3[CH:49]=[CH:48][C:20]([CH2:21][CH:22]4[S:26][C:25](=[O:27])[N:24]([C:28]([C:41]5[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=5)([C:35]5[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=5)[C:29]5[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=5)[C:23]4=[O:47])=[CH:19][CH:18]=3)=[N:12][C:7]2=[CH:6][CH:5]=1)[CH3:2]

Participants

6

Reactant 4

HCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 28181265-(4-Hydroxybenzyl)-3-triphenylmethylthiazolidine-2,4-dioneHCID 10560253(5-ethoxy-3-methyl-3H-imidazo[4,5-b]pyridin-2-yl)methanol

Product 1

HCID 105562575-{4-(5-Ethoxy-3-methylimidazo[5,4-b]pyridin-2-ylmethoxy)benzyl}-3-triphenylmethylthiazolidine-2,4-dioneYield 88.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A procedure similar to that described in Preparation 4 was repeated, except that 1.00 g of 5-ethoxy-2-hydroxymethyl-3-methyl-3H-imidazo[4,5-b]pyridine (prepared as described in Preparation 98), 2.25 g of 5-(4-hydroxybenzyl)-3-triphenylmethylthiazolidine-2,4-dione, 1.2 ml of tributylphosphine, 1.22 g of 1,1'-(azodicarbonyl)dipiperidine and 60 ml of toluene were used, and that the 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 2.81 g of the title compound, melting at 88-100° C. (softening).

Workup

  1. customA procedure similar to that described in Preparation 4
  2. customthat the product was purified by column chromatography through silica gel
  3. additionby volume mixture of hexane and ethyl acetate as the eluent

Sources & evidence

ORD record
ord-eca3260e1bb6491a8449ab817b27fe69
Source dataset
uspto-grants-1999_11
Patent number
US05977365

Reaction notes

Loading…