Imidazo(4,5-b)pyridine → HCID 68764916, compound

HRID 2391732Notes

Reaction equation

HRID 2391732 reaction equation
[NH:1]1[C:9]2[C:4](=[N:5][CH:6]=[CH:7][CH:8]=2)[N:3]=[CH:2]1.Cl[C:11]1([C:17]([O:19][CH3:20])=[O:18])[C:15](=[O:16])[CH:14]=[CH:13][S:12]1>C(Cl)(Cl)Cl>[CH3:20][O:19][C:17]([C:11]1[S:12][C:13]([N:3]2[C:4]3=[N:5][CH:6]=[CH:7][CH:8]=[C:9]3[N:1]=[CH:2]2)=[CH:14][C:15]=1[OH:16])=[O:18]

Participants

4

Reactant 2

HCID 67504Imidazo(4,5-b)pyridineHCID 15588102Methyl 2-chloro-3-oxo-2,3-dihydrothiophene-2-carboxylate

Product 1

HCID 68764916HCID 68764916, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

In a similar manner as described for example C6, 30.0 g of 1H-imidazo[4,5-b]pyridine and 19.26 g of methyl 2-chloro-3-oxo-2,3-dihydrothiophene-2-carboxylate in 2 l chloroform give 3-hydroxy-5-imidazo[4,5-b]pyridin-3-yl-thiophene-2-carboxylic acid methyl ester (compound C8b) and the crude title compounds as an isomeric mixture which was used for the next step without further purification (example B5). The structural assignment of compound C8b was unequivocally established by two-dimensional 1H NMR experiment (NOESY, COSY).

Sources & evidence

ORD record
ord-ccef5bf696ee4e949f4757dd5f025d67
Source dataset
uspto-grants-2012_09
Patent number
US08273890B2

Reaction notes

Loading…