Methyl 2-chloro-3-oxo-2,3-dihydrothiophene-2-carboxylate → methyl 3-hydroxy-5-(6-methoxy-3H-imidazo[4,5-c]pyridin-3-yl)thiophene-2-carboxylate

HRID 2391729Notes

Reaction equation

HRID 2391729 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[CH:7][C:6]2[N:9]=[CH:10][NH:11][C:5]=2[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>C(Cl)(Cl)Cl>[OH:18][C:17]1[CH:16]=[C:15]([N:9]2[C:6]3[CH:7]=[N:8][C:3]([O:2][CH3:1])=[CH:4][C:5]=3[N:11]=[CH:10]2)[S:14][C:13]=1[C:19]([O:21][CH3:22])=[O:20]

Participants

4

Reactant 2

HCID 15588102Methyl 2-chloro-3-oxo-2,3-dihydrothiophene-2-carboxylateHCID 178486902HCID 178486902, compound

Product 1

HCID 68768518methyl 3-hydroxy-5-(6-methoxy-3H-imidazo[4,5-c]pyridin-3-yl)thiophene-2-carboxylate

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 2.00 g of 6-methoxy-1H-imidazo[4,5-c]pyridine in 50 ml of chloroform were added 1.25 g of methyl 2-chloro-3-oxo-2,3-dihydrothiophene-2-carboxylate in portions and the reaction mixture was stirred for 120 h at room temperature. The reaction mixture was washed with water (3×50 ml) and the organic layer was dried and concentrated under vacuum. The residue was recrystallized from methanol to yield the title compounds as an isomeric mixture.

Workup

  1. washThe reaction mixture was washed with water (3×50 ml)
  2. customthe organic layer was dried
  3. concentrationconcentrated under vacuum
  4. customThe residue was recrystallized from methanol

Sources & evidence

ORD record
ord-032bbd81f559427cba195a42ddf4d17a
Source dataset
uspto-grants-2012_09
Patent number
US08273890B2

Reaction notes

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