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

HRID 1953645Notes

Reaction equation

HRID 1953645 reaction equation
[CH3:1][N:2]1[C:6]2=[N:7][CH:8]=[CH:9][CH:10]=[C:5]2[N:4]=[C:3]1[CH2:11][O:12][C:13]1[CH:45]=[CH:44][C:16]([CH2:17][CH:18]2[S:22][C:21](=[O:23])[N:20](C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[C:19]2=[O:43])=[CH:15][CH:14]=1>[Pd].CO>[CH3:1][N:2]1[C:6]2=[N:7][CH:8]=[CH:9][CH:10]=[C:5]2[N:4]=[C:3]1[CH2:11][O:12][C:13]1[CH:14]=[CH:15][C:16]([CH2:17][CH:18]2[S:22][C:21](=[O:23])[NH:20][C:19]2=[O:43])=[CH:44][CH:45]=1

Participants

4

Reactant 1

HCID 107463025-[4-(3-Methylimidazo[5,4-b]pyridin-2-ylmethoxy)benzyl]-3-triphenylmethylthiazolidine-2,4-dione

Product 1

HCID 97994005-{4-(3-Methylimidazo[5,4-b]pyridin-2-ylmethoxy)-benzyl}thiazolidine-2,4-dioneYield 25.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A procedure similar to that described in Example 6 was repeated, except that 500 mg of 5-[4-(3-methylimidazo[5,4-b]pyridin-2-ylmethoxy)benzyl]-3-triphenylmethylthiazolidine-2,4-dione (prepared as described in Preparation 16), 1 g of 10% w/w palladium-on-charcoal and 100 ml of methanol were used, to give 77 mg of the title compound, melting at 223-225° C.

Sources & evidence

ORD record
ord-540a308f94204d36b1c41a2cd0baf8db
Source dataset
uspto-grants-2000_09
Patent number
US06117893

Reaction notes

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