Ethyl Acetate → 8-Ethyl-1-methyl-thienyl[3',4':6,5]dipyrido[2,3-b:3',2'-f]azepine

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Reaction Steps

To a solution of 8-ethyl-thienyl[3',4':6,5]dipyrido[2,3-b:3',2'-f]azepine (0.025 g) in tetrahydrofuran (2 mL) cooled to -78° C. was added lithium diisopropylamide (1.5M in cyclohexane, 0.1 mL). After 10 minutes, iodomethane (2 drops) was added, and the mixture was allowed to warm to room temperature. The mixture was diluted with ethyl acetate, washed with water, dried, filtered and evaporated. The residue was dissolved in tetrahydrofuran (2 mL) cooled to -78° C., and lithium diisopropylamide (1.5M in cyclohexane, 0.1 mL) was added. After 10 minutes, iodomethane (0.05 mL) was added, and the mixture was allowed to warm to room temperature. The mixture was diluted with ethyl acetate, washed with water, dried, filtered and evaporated. The residue was fractionated by HPLC to give 8-ethyl-1-methyl-thienyl[3',4':6,5]dipyrido[2,3-b:3',2'-f]azepine (0.010 g) mp 106-108° C. and 8-ethyl-1,3-dimethyl-thienyl[3',4':6,5]dipyrido[2,3-b:3',2'-f]azepine (0.003 g) mp 176-178° C.

Provenance & Evidence