Sodium Iodide → 2-Amino-3-benzoyl-6-methyl-4,5,6,7-tetrahydrothieno[2,3-c]pyridine

HRID 566952Notes

Reaction equation

[NH2:1][C:2]1[S:10][C:5]2[CH2:6][NH:7][CH2:8][CH2:9][C:4]=2[C:3]=1[C:11](=[O:18])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.CI.[C:21](=O)([O-])[O-].[K+].[K+].[I-].[Na+]>CN(C)C=O.O>[NH2:1][C:2]1[S:10][C:5]2[CH2:6][N:7]([CH3:21])[CH2:8][CH2:9][C:4]=2[C:3]=1[C:11](=[O:18])[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

Conditions

Temperature: 65 °C

Procedure

2-Amino-3-benzoyl-4,5,6,7-tetrahydrothieno[2,3-c]pyridine (2 mmol), as prepared in Example 8, and methyl iodide (3 mmol) were dissolved in dry dimethyformamide (20 mL). Finely ground anhydrous potassium carbonate (1.9 g) and sodium iodide (0.2 g) were added to the solution and the resulting mixture was warmed to 65° C. overnight under nitrogen. After this period (TLC control), the reaction mixture was cooled, diluted with water, extracted with diethyl ether (3×50 mL), and dried on sodium sulfate. The crude product was isolated and then purified by column chromatography eluting with ethyl acetate and petroleum ether solutions to give the desired compound. (m.p. 164-165° C.; 77% yield).

Workup

waitAfter this period (TLC control)
temperaturethe reaction mixture was cooled
extractionextracted with diethyl ether (3×50 mL)
customdried on sodium sulfate
customThe crude product was isolated
custompurified by column chromatography
washeluting with ethyl acetate and petroleum ether solutions

Sources & evidence

ORD record: ord-9c38d1985e4d4a609bc724e209c0972a
Source dataset: uspto-grants-2001_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06177444B1

Reaction notes

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