Hydrochloric Acid → 4-(5-Methoxy-7-phenylimidazo[1,2-a]pyridin-3-yl)thiophene-2-carboxylic acid

HRID 1253569Notes

Reaction equation

HRID 1253569 reaction equation
[CH3:1][O:2][C:3]1[N:8]2[C:9]([C:12]3[CH:13]=[C:14]([C:17]([O:19]C)=[O:18])[S:15][CH:16]=3)=[CH:10][N:11]=[C:7]2[CH:6]=[C:5]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:4]=1.[OH-].[Na+].Cl>CO.O>[CH3:1][O:2][C:3]1[N:8]2[C:9]([C:12]3[CH:13]=[C:14]([C:17]([OH:19])=[O:18])[S:15][CH:16]=3)=[CH:10][N:11]=[C:7]2[CH:6]=[C:5]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:4]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 58404681Methyl 4-(5-methoxy-7-phenylimidazo[1,2-a]pyridin-3-yl)thiophene-2-carboxylate

Product 1

HCID 584046854-(5-Methoxy-7-phenylimidazo[1,2-a]pyridin-3-yl)thiophene-2-carboxylic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of methyl 4-(5-methoxy-7-phenylimidazo[1,2-a]pyridin-3-yl)thiophene-2-carboxylate (94 mg, 0.26 mmol) in methanol (10 ml) and water (0.5 ml) was added a 5M aqueous solution of sodium hydroxide (0.50 ml, 2.5 mmol). The reaction mixture was heated to 70° C. After 1 h the reaction mixture was cooled and quenched with a 1N solution of hydrochloric acid (2.5 ml, 2.5 mmol), and then partially concentrated to precipitate yellow solids. The solids were washed with water and dried under vacuum to give 4-(5-methoxy-7-phenylimidazo[1,2-a]pyridin-3-yl)thiophene-2-carboxylic acid. LRMS (ESI) calculated for C19H15N2O3S [M+H]+, 351.1 found 351.0.

Workup

  1. temperatureAfter 1 h the reaction mixture was cooled
  2. concentrationpartially concentrated
  3. customto precipitate yellow solids
  4. washThe solids were washed with water
  5. customdried under vacuum

Sources & evidence

ORD record
ord-e28e246aaeba445cad2f4d4608094710
Source dataset
uspto-grants-2013_06
Patent number
US08455477B2

Reaction notes

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