2,2,6,6-Tetramethylpiperidine → methyl 3-hydroxy-5-(5-methoxy-3H-imidazo[4,5-b]pyridin-3-yl)thiophene-2-carboxylate

HRID 2391734Notes

Reaction equation

HRID 2391734 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][CH:4]=1.Cl[C:13]1([C:19]([O:21][CH3:22])=[O:20])[C:17](=[O:18])[CH:16]=[CH:15][S:14]1.CC1(C)CCCC(C)(C)N1>C(Cl)(Cl)Cl>[OH:18][C:17]1[CH:16]=[C:15]([N:9]2[C:7]3=[N:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=[C:6]3[N:11]=[CH:10]2)[S:14][C:13]=1[C:19]([O:21][CH3:22])=[O:20]

Participants

5

Reactant 3

HCID 130352,2,6,6-TetramethylpiperidineHCID 15588102Methyl 2-chloro-3-oxo-2,3-dihydrothiophene-2-carboxylateHCID 21683295HCID 21683295, compound

Product 1

HCID 68764082methyl 3-hydroxy-5-(5-methoxy-3H-imidazo[4,5-b]pyridin-3-yl)thiophene-2-carboxylate

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

In a similar manner as described for example C2, 8.54 g of the above-synthesized 5-methoxy-1H-imidazo[4,5-b]pyridine and 4.46 g of methyl 2-chloro-3-oxo-2,3-dihydrothiophene-2-carboxylate and 13.07 g of 2,2,6,6-tetramethylpiperidine in 620 ml chloroform yield the title compounds as an isomeric mixture which was used for the next step (example B7) without further purification.

Sources & evidence

ORD record
ord-d39ca731186d4b25b4be26dc43511163
Source dataset
uspto-grants-2012_09
Patent number
US08273890B2

Reaction notes

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