Water → N-(4-chlorobenzyl)-2-iodo-4-methyl-7-oxo-4,7-dihydrothieno[3,2-b]pyridine-6-carboxamide

HRID 982705Notes

Reaction equation

HRID 982705 reaction equation
[Cl:1][C:2]1[CH:22]=[CH:21][C:5]([CH2:6][NH:7][C:8]([C:10]2[C:11]([OH:20])=[C:12]3[S:18][C:17]([I:19])=[CH:16][C:13]3=[N:14][CH:15]=2)=[O:9])=[CH:4][CH:3]=1.[C:23]([O-])([O-])=O.[K+].[K+].CI.O>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][NH:7][C:8]([C:10]2[C:11](=[O:20])[C:12]3[S:18][C:17]([I:19])=[CH:16][C:13]=3[N:14]([CH3:23])[CH:15]=2)=[O:9])=[CH:21][CH:22]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 178522890HCID 178522890, compound

Product 1

HCID 22563223N-(4-chlorobenzyl)-2-iodo-4-methyl-7-oxo-4,7-dihydrothieno[3,2-b]pyridine-6-carboxamideYield 74%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

To a stirring mixture of N-(4-chlorobenzyl)-7-hydroxy-2-iodothieno[3,2-b]pyridine-6-carboxamide (0.50 g, 1.12 mmol) in DMF (20 mL) in a pressure tube was added K2CO3 (0.31 g, 2.25 mmol). To the resulting suspension was added CH3I (0.335g, 2.36 mmol), the vessel capped and heated at 90° C. for 16 h. The resulting dark suspension was cooled to ambient temperature and poured into H2O (100 mL). The aqueous solution was extracted with CH2Cl2 (3×100 mL). The organic layers were combined, dried over MgSO4 and solvent removed to afford 0.38 g title compound as a yellow solid.

Workup

  1. customthe vessel capped
  2. temperatureThe resulting dark suspension was cooled to ambient temperature
  3. extractionThe aqueous solution was extracted with CH2Cl2 (3×100 mL)
  4. dry with materialdried over MgSO4 and solvent
  5. customremoved

Sources & evidence

ORD record
ord-9f071d17ffe142288014442a7b2b52da
Source dataset
uspto-grants-2005_03
Patent number
US06861438B2

Reaction notes

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