[S:1]1[C:9]2[CH2:8][CH2:7][NH:6][C:5](=[O:10])[C:4]=2[CH:3]=[CH:2]1.I[C:12]1[CH:13]=[N:14][CH:15]=[CH:16][C:17]=1[CH3:18].P([O-])([O-])([O-])=O.[K+].[K+].[K+]>[Cu](I)I.O1CCOCC1>[CH3:18][C:17]1[CH:16]=[CH:15][N:14]=[CH:13][C:12]=1[N:6]1[CH2:7][CH2:8][C:9]2[S:1][CH:2]=[CH:3][C:4]=2[C:5]1=[O:10]
Using analogous reaction conditions as described in example 1, 6,7-dihydro-5H-thieno[3,2-c]pyridin-4-one (I-7d: 100 mg, 0.6527 mmol) was reacted with 3-iodo-4-methyl-pyridine (171.5 mg, 0.7832 mmol), 1,4-dioxane (20 mL), copper iodide (9.7 mg, 0.0652 mmol), trans-N,N′-dimethyl-cyclohexyl-1,2-diamine (27.8 mg, 0.1958 mmol) and potassium phosphate (346.3 mg, 1.6318 mmol) to afford the crude product. Purification by column chromatography on silica gel (2% methanol in CHCl3) afforded 90 mg of the product (56.2% yield).
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