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

HRID 55485Notes

Reaction equation

HRID 55485 reaction equation
[CH2:1]([N:3]1[C:7]2=[N:8][CH:9]=[CH:10][CH:11]=[C:6]2[N:5]=[C:4]1[CH2:12][OH:13])[CH3:2].O[C:15]1[CH:47]=[CH:46][C:18]([CH2:19][CH:20]2[S:24][C:23](=[O:25])[N:22]([C:26]([C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[C:21]2=[O:45])=[CH:17][CH:16]=1.C(P(CCCC)CCCC)CCC.N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O>C1C=CC=CC=1>[CH2:1]([N:3]1[C:7]2=[N:8][CH:9]=[CH:10][CH:11]=[C:6]2[N:5]=[C:4]1[CH2:12][O:13][C:15]1[CH:47]=[CH:46][C:18]([CH2:19][CH:20]2[S:24][C:23](=[O:25])[N:22]([C:26]([C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)([C:33]3[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=3)[C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[C:21]2=[O:45])=[CH:17][CH:16]=1)[CH3:2]

Participants

6

Reactant 4

HCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 28181265-(4-Hydroxybenzyl)-3-triphenylmethylthiazolidine-2,4-dioneHCID 10511506(3-ethyl-3H-imidazo[4,5-b]pyridin-2-yl)methanol

Product 1

HCID 118020545-{4-(3-Ethylimidazo[5,4-b]pyridin-2-ylmethoxy)-benzyl}-3-triphenylmethylthiazolidine-2,4-dione

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

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).

Workup

  1. customA procedure similar to that described in Preparation 4

Sources & evidence

ORD record
ord-14ff9859154a45bfa89f4ab9f727069e
Source dataset
uspto-grants-1997_04
Patent number
US05624935

Reaction notes

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