4-Toluenesulfonyl chloride → HCID 90388503, compound
Reaction equation
[S:1]1[C:9]2[C:8](=[O:10])[CH2:7][N:6]=[CH:5][C:4]=2[CH:3]=[CH:2]1.[H-].[Na+].[S:13](Cl)([C:16]1[CH:22]=[CH:21][C:19]([CH3:20])=[CH:18][CH:17]=1)(=[O:15])=[O:14]>C1COCC1>[CH3:20][C:19]1[CH:21]=[CH:22][C:16]([S:13]([O:10][C:8]2[C:9]3[S:1][CH:2]=[CH:3][C:4]=3[CH:5]=[N:6][CH:7]=2)(=[O:15])=[O:14])=[CH:17][CH:18]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of thieno[3,2-c]pyridin-7(6H)-one (110 mg, 0.728 mmol, 1.0 equiv) in THF (5.00 mL) was added NaH (35 mg, 0.873 mmol, 1.2 equiv) followed by TsCl (180 mg, 0.946 mmol, 1.3 equiv). The reaction mixture was stirred at rt for 2 h, then quenched with water and extracted with ethyl acetate. Purification by column chromatography using 20% ethyl acetate in hexanes elution gave 180 mg of a white solid, 81%.