2-Chloroacetophenone → 3-Thiocyano-2-methyl-7-phenacylpyrrolo[2,3-b]pyridine hydrochloride
Reaction equation
[S:1]([C:4]1[C:12]2[C:7](=[N:8][CH:9]=[CH:10][CH:11]=2)[NH:6][C:5]=1[CH3:13])[C:2]#[N:3].[CH2:14]([Cl:23])[C:15]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:16]>C(#N)C.CN(C)C=O>[ClH:23].[S:1]([C:4]1[C:12]2[C:7]([N:8]([CH2:14][C:15]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[O:16])[CH:9]=[CH:10][CH:11]=2)=[N:6][C:5]=1[CH3:13])[C:2]#[N:3]Participants
4
Procedure
A solution of 100 mg (0.53 mmol) of 3-thiocyano-2-methyl pyrrolo [2,3-b]pyridine and 122 mg (0.79 mmol) of phenacyl chloride in 3 ml acetonitrile: dimethylformamide 2:1 was warmed at 70° C. for 36 h. The reaction mixture was cooled to room temperature and the acetonitrile was evaporated. To the residue was added 10 ml diethyl ether. The precipitated product was filtered off and washed with acetonitrile giving 37 mg (23%) of the title compound.