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

HRID 1599336Notes

Reaction equation

HRID 1599336 reaction equation
[CH:1]([O:4][C:5]1[N:10]=[C:9]2[N:11]([CH3:16])[C:12]([CH2:14][OH:15])=[N:13][C:8]2=[CH:7][CH:6]=1)([CH3:3])[CH3:2].O[C:18]1[CH:50]=[CH:49][C:21]([CH2:22][CH:23]2[S:27][C:26](=[O:28])[N:25]([C:29]([C:42]3[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=3)([C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)[C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[C:24]2=[O:48])=[CH:20][CH:19]=1.C(P(CCCC)CCCC)CCC.N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O>C1(C)C=CC=CC=1>[CH:1]([O:4][C:5]1[N:10]=[C:9]2[N:11]([CH3:16])[C:12]([CH2:14][O:15][C:18]3[CH:50]=[CH:49][C:21]([CH2:22][CH:23]4[S:27][C:26](=[O:28])[N:25]([C:29]([C:42]5[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=5)([C:36]5[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=5)[C:30]5[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=5)[C:24]4=[O:48])=[CH:20][CH:19]=3)=[N:13][C:8]2=[CH:7][CH:6]=1)([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 28181265-(4-Hydroxybenzyl)-3-triphenylmethylthiazolidine-2,4-dioneHCID 108228683h-Imidazo[4,5-b]pyridine-2-methanol,3-methyl-5-(1-methylethoxy)-

Product 1

HCID 107945465-{4-(5-Isopropoxy-3-methylimidazo(5,4-b]pyridin-2-ylmethoxy)benzyl}-3-triphenylmethylthiazolidine-2,4-dioneYield 85.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A procedure similar to that described in Preparation was repeated, except that 0.33 g 5-isopropoxy-2-hydroxymethyl-3-methylimidazo[5,4-b]pyridine (prepared as described in Preparation 102), 0.69 g of 5-(4-hydroxybenzyl)-3-triphenylmethylthiazolidine-2,4-dione, 0.37 ml of tributylphosphine, 0.38 g of 1,1'-(azodicarbonyl)dipiperidine and 20 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 0.85 g of the title compound, melting at 90°-100° C. (softening).

Workup

  1. customA procedure similar to that described in Preparation
  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-716a1a60b83849beb75ffb7dd0525a22
Source dataset
uspto-grants-1998_04
Patent number
US05739345

Reaction notes

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