Methyl iodide → HCID 22563226, compound

HRID 982708Notes

Reaction equation

HRID 982708 reaction equation
CI.[CH:3]([C:5]1[S:13][C:12]2[C:11](=[O:14])[C:10]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:9][NH:8][C:7]=2[CH:6]=1)=[O:4].[C:20](=O)([O-])[O-].[K+].[K+]>CN(C=O)C.O>[CH:3]([C:5]1[S:13][C:12]2[C:11](=[O:14])[C:10]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:9][N:8]([CH3:20])[C:7]=2[CH:6]=1)=[O:4]

Participants

6

Reactant 3

HCID 6328Methyl iodide2×HCID 11430Potassium CarbonateHCID 22563214HCID 22563214, compound

Product 1

HCID 22563226HCID 22563226, compoundYield 41.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Methyl iodide (1.2 mL, 19.3 mmol) was added to a mixture of ethyl 2-formyl-7-oxo-4,7-dihydrothieno[3,2-b]pyridine-6-carboxylate (3.0 g, 11.9 mmol), potassium carbonate (2.5 g, 18.1 mmol) in DMF (30 mL) at 0° C. After the addition of methyl iodide, the mixture was stirred at room temperature for 1 hr. The mixture was diluted with water (40 mL), stirred at room temperature for 15 minutes, and then filtered. The collected solid was washed with water and dried in vacuo, leaving a solid (1.3 g, 41%). The aqueous phase was extracted with methylene chloride (2×50 mL). The organic layers were combined, washed with water (50 mL) and brine (50 mL), and dried over magnesium sulfate. Removal of the solvent gave a second crop of product (0.34 g).

Workup

  1. stirringstirred at room temperature for 15 minutes
  2. filtrationfiltered
  3. washThe collected solid was washed with water
  4. customdried in vacuo

Sources & evidence

ORD record
ord-5eb607a38cab47d08c7bed645601be0b
Source dataset
uspto-grants-2005_03
Patent number
US06861438B2

Reaction notes

Loading…