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

HRID 2391724Notes

Reaction equation

HRID 2391724 reaction equation
[NH:1]1[C:9]2[CH:8]=[CH:7][N:6]=[CH:5][C:4]=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>ClCCl>[OH:16][C:15]1[CH:14]=[C:13]([N:3]2[C:4]3[CH:5]=[N:6][CH:7]=[CH:8][C:9]=3[N:1]=[CH:2]2)[S:12][C:11]=1[C:17]([O:19][CH3:20])=[O:18]

Participants

4

Reactant 2

HCID 15588102Methyl 2-chloro-3-oxo-2,3-dihydrothiophene-2-carboxylateHCID 178419860HCID 178419860, compound

Product 1

HCID 68765327methyl 3-hydroxy-5-(3H-imidazo[4,5-c]pyridin-3-yl)thiophene-2-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 6 g of 1H-imidazo[4,5-c]pyridine in 300 ml of anhydrous dichloromethane is slowly added a solution of 4.8 g of methyl 2-chloro-3-oxo-2,3-dihydrothiophene-2-carboxylate. The reaction mixture is stirred for 14 h at room temperature. The solvent is removed under reduced pressure and the residue is purified by flash chromatography [silica gel, elution gradient of toluene/ethyl acetate/acetic acid, 80/20/1 (v/v/v)] to 30/70/1 (v/v/v) to give the separated title compounds along with a small fraction of the isomeric mixture.

Workup

  1. customThe solvent is removed under reduced pressure
  2. customthe residue is purified by flash chromatography [silica gel, elution gradient of toluene/ethyl acetate/acetic acid, 80/20/1 (v/v/v)] to 30/70/1 (v/v/v)
  3. customto give the
  4. customseparated title compounds along with a small fraction of the isomeric mixture

Sources & evidence

ORD record
ord-da114062ee334390b0aad5073c7b27c8
Source dataset
uspto-grants-2012_09
Patent number
US08273890B2

Reaction notes

Loading…