Imidazole → 2-Imidazol-1-yl-4-(4-methoxy-benzylamino)-thieno[3,2-c]pyridine-7-carbonitrile

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Reaction Steps

To an oven dried Schlenk tube was added CuI (0.0057 g, 0.030 mmol), imidazole (0.097 g, 1.42 mmol), Cs2CO3 (0.405 g, 1.25 mmol). The tube was evacuated and purged to argon 5 times. Under argon, the tube was supplied with 2-iodo-4-(4-methoxy-benzylamino)-thieno[3,2-c]pyridine-7-carbonitrile 27 (0.25 g, 0.59 mmol) trans-1,2-cyclohexanediamine (0.014 mL, 0.12 mmol), and dioxane (1 mL). The reaction contents were briefly evacuated and the vessel purged to argon 3 times, then sealed and brought to 110° C. with stirring. After 24 h, 20 mL of CH2Cl2 were added to the cooled reaction. The mixture was filtered and solvents removed in vacuo. Silica gel column chromatography (eluent: 3% MeOH in CH2Cl2) provided 0.12 g of 37. 1H NMR (400 MHz, d6-DMSO) δ 8.57 (t, J=6 Hz, 1H), 8.47 (s, 1H), 8.23 (bs, 1H), 8.00 (s, 1H), 7.71 (bs, 1H), 7.31 (d, J=8 Hz, 2H), 7.21 (bs, 1H), 6.91 (d, J=8 Hz, 2H), 3.74 (s, 3H).

Provenance & Evidence