[NH2:1][C:2]1[S:6][C:5]2[CH2:7][CH2:8][CH2:9][C:4]=2[C:3]=1[C:10]#[N:11].[CH:12]1([C:15](=[O:21])[CH:16]=[C:17](OC)[CH3:18])[CH2:14][CH2:13]1.C1(C)C=CC(S(O)(=O)=O)=CC=1.[Sn](Cl)(Cl)(Cl)Cl>C1(C)C=CC=CC=1>[NH2:11][C:10]1[C:3]2[C:4]3[CH2:9][CH2:8][CH2:7][C:5]=3[S:6][C:2]=2[N:1]=[C:17]([CH3:18])[C:16]=1[C:15]([CH:12]1[CH2:14][CH2:13]1)=[O:21]To a stirred solution of 0.30 g (1.83 mmol) of 2-amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile in 6 ml toluene was added 0.30 g (2.14 mmol) 1-cyclopropyl-3-methoxy-but-2-en-1-one and 3 mg of p-toluenesulfonic acid. The mixture was heated at reflux for 2 hours, concentrated in vacuo, partitioned between ethyl acetate and water. The combined organic phases were dried over sodium sulfate and evaporated to dryness. The residue was taken up in n-butyl acetate 6 ml and 1.018 g (3.91 mmol) tin (IV) chloride was heated under reflux for 30 minute and allowed to cool. The mixture was partitioned between aqueous sodium hydroxide and ethyl acetate. Flash chromatography (heptane/ethyl acetate 3:1) afforded 25 mg (5%) (4-amino-6-methyl-2,3-dihydro-1H-8-thia-7-aza-cyclopenta[a]inden-5-yl)-cyclopropyl-methanone as a white solid. ES-MS m/e (%): 273 (M+H+, 100).
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