Dimethylformamide → Ethyl 3,4-dimethyl-7-oxo-4,7-dihydrothieno[3,2-b]pyridine-6-carboxylate

HRID 23634Notes

Reaction equation

HRID 23634 reaction equation
[OH:1][C:2]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:6][N:5]=[C:4]2[C:13]([CH3:16])=[CH:14][S:15][C:3]=12.[CH3:17]N(C=O)C.C(=O)([O-])[O-].[K+].[K+].IC>O>[CH3:16][C:13]1[C:4]2[N:5]([CH3:17])[CH:6]=[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[C:2](=[O:1])[C:3]=2[S:15][CH:14]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 178469607HCID 178469607, compound

Product 1

HCID 22574379Ethyl 3,4-dimethyl-7-oxo-4,7-dihydrothieno[3,2-b]pyridine-6-carboxylate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

A 500 mL three-necked flask fitted with an overhead stirrer and argon inlet is charged with 21.9 g of ethyl 7-hydroxy-3-methylthieno[3,2-b]pyridine-6-carboxylate and 150 mL of DMF. The mixture is stirred while 25.5 g of powdered potassium carbonate is added in portions, then is cooled to 0° C. Iodomethane (15 mL) is added dropwise over 45 min, and the completed mixture is stirred vigorously and allowed to warm slowly as the ice in the bath melts. The following day, the mixture is diluted slowly with water to a final volume of 800 ml, and the resulting solid is filtered, washed well with water, and dried under vacuum to provide 17.2 g of the title compound as a brown crystalline solid. Flash chromatography of 12.2 g using 2-4% MeOH in CH2Cl2 affords 11.43 g of tan solid.

Workup

  1. customA 500 mL three-necked flask fitted with an overhead stirrer and argon inlet
  2. additionis added in portions
  3. filtrationthe resulting solid is filtered
  4. washwashed well with water
  5. customdried under vacuum

Sources & evidence

ORD record
ord-309f1323c795466d872c652481908237
Source dataset
uspto-grants-2005_02
Patent number
US06852731B2

Reaction notes

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