Acetic Acid → 4-bromothieno[2,3-c]pyridine

HRID 2283681Notes

Reaction equation

HRID 2283681 reaction equation
C(O)(=O)C.[Br:5][C:6]1[CH:11]=[N:10][CH:9]=[C:8]2[S:12][C:13](C([O-])=O)=[CH:14][C:7]=12>CN(C=O)C.C(OCC)(=O)C.C(=O)([O-])[O-].[Ag+2]>[Br:5][C:6]1[CH:11]=[N:10][CH:9]=[C:8]2[S:12][CH:13]=[CH:14][C:7]=12

Participants

6

Reactant 2

HCID 176Acetic AcidHCID 131733525HCID 131733525, compound

Product 1

HCID 185163464-bromothieno[2,3-c]pyridine

Reagents, catalysts & solvents 3

HCID 178418647HCID 178418647, compoundCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
120 °C

Procedure

Silver carbonate (28 mg) and acetic acid (0.006 ml) were added to a solution of 4-bromothieno[2,3-c]pyridine-2-carboxylate obtained in the above-described Step 1 (258 mg) in DMF (2.0 ml), and the reaction solution was stirred at 120° C. for 24 hours. The reaction solution was diluted with ethyl acetate and washed successively with an aqueous sodium bicarbonate solution and a saturated saline solution. After drying over anhydrous sodium sulfate, the solvent was evaporated under vacuum. The resultant residue was purified by column chromatography on silica gel (developing solvent:hexane-ethyl acetate) to obtain 4-bromothieno[2,3-c]pyridine.

Workup

  1. washwashed successively with an aqueous sodium bicarbonate solution
  2. dry with materialAfter drying over anhydrous sodium sulfate
  3. customthe solvent was evaporated under vacuum
  4. customThe resultant residue was purified by column chromatography on silica gel (developing solvent:hexane-ethyl acetate)

Sources & evidence

ORD record
ord-73a57001af7941ac8f7eb804063eef96
Source dataset
uspto-grants-2015_09
Patent number
US09145414B2

Reaction notes

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