Potassium Carbonate → Ethyl 4-chloro-3-hydroxy-6-methylthieno[3,2-c]pyridine-2-carboxylate

HRID 1513569Notes

Reaction equation

HRID 1513569 reaction equation
[Cl:1][C:2]1[C:7]([C:8]([O:10]CC)=O)=[C:6](Cl)[CH:5]=[C:4]([CH3:14])[N:3]=1.C(=O)([O-])[O-].[K+].[K+].[C:21]([O:25][CH2:26][CH3:27])(=[O:24])[CH2:22][SH:23]>C(#N)C.O.Cl>[Cl:1][C:2]1[C:7]2[C:8]([OH:10])=[C:22]([C:21]([O:25][CH2:26][CH3:27])=[O:24])[S:23][C:6]=2[CH:5]=[C:4]([CH3:14])[N:3]=1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 12185Ethyl ThioglycolateHCID 604813Ethyl 2,4-dichloro-6-methylnicotinate

Product 1

HCID 57860702Ethyl 4-chloro-3-hydroxy-6-methylthieno[3,2-c]pyridine-2-carboxylateYield 94%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

To a suspension of ethyl 2,4-dichloro-6-methylpyridine-3-carboxylate (10.0 g, 42.7 mmol) in acetonitrile (45 mL) were added potassium carbonate (8.85 g, 64.1 mmol) and ethyl thioglycolate (4.68 mL, 42.7 mmol), and the mixture was stirred for 15 hr under refluxing conditions. The reaction mixture was diluted with water (150 mL), 6N hydrochloric acid (15 mL) was added and the mixture was stirred for 30 min. The precipitated solid was collected by filtration, washed with water and ethanol-diisopropyl ether (1/1), and dried under reduced pressure to give the title compound (10.9 g, 94%) as a white powder.

Workup

  1. additionwas added
  2. stirringthe mixture was stirred for 30 min
  3. filtrationThe precipitated solid was collected by filtration
  4. washwashed with water and ethanol-diisopropyl ether (1/1)
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-c922d66ef8c3425bbd9440cfcd5be4b1
Source dataset
uspto-grants-2012_07
Patent number
US08217176B2

Reaction notes

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