Methyl 2-chloro-3-oxo-2,3-dihydrothiophene-2-carboxylate → methyl 5-(5,6-dimethoxy-3H-imidazo[4,5-b]pyridin-3-yl)-3-hydroxythiophene-2-carboxylate

HRID 2391731Notes

Reaction equation

HRID 2391731 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[C:7]2[N:9]=[CH:10][NH:11][C:6]2=[CH:5][C:4]=1[O:12][CH3:13].Cl[C:15]1([C:21]([O:23][CH3:24])=[O:22])[C:19](=[O:20])[CH:18]=[CH:17][S:16]1>C(Cl)(Cl)Cl>[CH3:1][O:2][C:3]1[N:8]=[C:7]2[N:9]([C:17]3[S:16][C:15]([C:21]([O:23][CH3:24])=[O:22])=[C:19]([OH:20])[CH:18]=3)[CH:10]=[N:11][C:6]2=[CH:5][C:4]=1[O:12][CH3:13]

Participants

4

Reactant 2

HCID 15588102Methyl 2-chloro-3-oxo-2,3-dihydrothiophene-2-carboxylateHCID 687649905,6-Dimethoxy-3h-imidazo[4,5-b]pyridine

Product 1

HCID 68767999methyl 5-(5,6-dimethoxy-3H-imidazo[4,5-b]pyridin-3-yl)-3-hydroxythiophene-2-carboxylate

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

In a similar manner as described for example C6, 1.50 g of the above-synthesized 5,6-dimethoxy-1H-imidazo[4,5-b]pyridine and 0.81 g of methyl 2-chloro-3-oxo-2,3-dihydrothiophene-2-carboxylate in 40 ml chloroform yield the title compounds as an isomeric mixture which was used for the next step without further purification (example B4).

Sources & evidence

ORD record
ord-ce6316acc2744d7dbda5a6135e93ff19
Source dataset
uspto-grants-2012_09
Patent number
US08273890B2

Reaction notes

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