Sodium Carbonate → Methyl 5-(pyridin-4-yl)thiophene-2-carboxylate

HRID 278554Notes

Reaction equation

HRID 278554 reaction equation
Br[C:2]1[S:6][C:5]([C:7]([O:9][CH3:10])=[O:8])=[CH:4][CH:3]=1.[N:11]1[CH:16]=[CH:15][C:14](OB(O)O)=[CH:13][CH:12]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(COC)OC.C(OCC)(=O)C>[N:11]1[CH:16]=[CH:15][C:14]([C:2]2[S:6][C:5]([C:7]([O:9][CH3:10])=[O:8])=[CH:4][CH:3]=2)=[CH:13][CH:12]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 605713Methyl 5-bromothiophene-2-carboxylateHCID 218058124-Pyridylboric acid

Product 1

HCID 21928559Methyl 5-(pyridin-4-yl)thiophene-2-carboxylateYield 54.2%

Reagents, catalysts & solvents 2

HCID 80711,2-DimethoxyethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of methyl 5-bromo-2-thiophenecarboxylate (884 mg), 4-pyridyl boric acid (500 mg), tetrakistriphenylphosphine palladium(0) (250 mg) in dimethoxyethane (15 ml) was added 2 M sodium carbonate solution (4 ml) and the solution was heated for 15 hours under reflux. The reaction solution was diluted with ethyl acetate and the organic layer was separated, washed with water and extracted with 1 N hydrochloric acid. The extract was made alkaline with sodium hydroxide solution and extracted with ethyl acetate. The extract was dried and concentrated to give pale yellow solid of methyl 5-(4-pyridyl)-2-thiophenecarboxylate (428 mg).

Workup

  1. temperaturethe solution was heated for 15 hours
  2. temperatureunder reflux
  3. customthe organic layer was separated
  4. washwashed with water
  5. extractionextracted with 1 N hydrochloric acid
  6. extractionextracted with ethyl acetate
  7. customThe extract was dried
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-ea864b6b5fcf42098a526fd3634311dd
Source dataset
uspto-grants-2002_03
Patent number
US06359134B1

Reaction notes

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