Hydrochloric Acid → 3-(4-Bromo-phenyl)-4-hydroxy-6-oxo-6,7-dihydro-thieno[2,3-b]pyridine-5-carboxylic acid ethyl ester

HRID 1244167Notes

Reaction equation

HRID 1244167 reaction equation
C(O[C:4]([C:6]1[C:10]([C:11]2[CH:16]=[CH:15][C:14]([Br:17])=[CH:13][CH:12]=2)=[CH:9][S:8][C:7]=1[NH:18][C:19](=[O:26])[CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])=[O:5])C.[H-].[Na+].Cl>CN(C=O)C>[CH2:24]([O:23][C:21]([C:20]1[C:19](=[O:26])[NH:18][C:7]2[S:8][CH:9]=[C:10]([C:11]3[CH:12]=[CH:13][C:14]([Br:17])=[CH:15][CH:16]=3)[C:6]=2[C:4]=1[OH:5])=[O:22])[CH3:25]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 696073284-(4-Bromo-phenyl)-2-(2-ethoxycarbonyl-acetylamino)-thiophene-3-carboxylic acid ethyl ester

Product 1

HCID 547275683-(4-Bromo-phenyl)-4-hydroxy-6-oxo-6,7-dihydro-thieno[2,3-b]pyridine-5-carboxylic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-(4-bromo-phenyl)-2-(2-ethoxycarbonyl-acetylamino)-thiophene-3-carboxylic acid ethyl ester (4.98 g, 11.3 mmol) in DMF (30 mL) at 0° C. was added a dispersion of sodium hydride in mineral oil (60%, 2.73 g, 68.2 mmol). After warming to ambient temperature the reaction was stirred overnight. Aqueous HCl (1.2 M, 100 mL) was added while cooling the mixture to 0° C. After stirring 1 h. the mixture was filtered and washed with H2O and hexanes giving the titled compound (2.85 g, 64%) as a gray solid.

Workup

  1. temperaturewhile cooling the mixture to 0° C
  2. stirringAfter stirring 1 h. the mixture
  3. filtrationwas filtered
  4. washwashed with H2O and hexanes giving the titled compound (2.85 g, 64%) as a gray solid

Sources & evidence

ORD record
ord-f65b422f698440b0957b0b1865eaac72
Source dataset
uspto-grants-2006_10
Patent number
US07119205B2

Reaction notes

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