Methyl iodide → 4-(4-chlorophenyl)-2-iodo-7-methyl-4,5,6,7-tetrahydro-8H-thieno[2,3-e]azepin-8-one

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Reaction Conditions

Reaction Steps

To a solution of 4-(4-chlorophenyl)-2-iodo-4,5,6,7-tetrahydro-8H-thieno[2,3-c]azepin-8-one (95.0 mg, 0.235 mmol, prepared in an analogous manner as described in Example 33) in tetrahydrofuran (8.6 mL) at −78° C. under an atmosphere of argon was added LiHMDS in hexane (1 M, 0.259 mL, 0.259 mmol). After stirring at −78° C. for 5 min, methyl iodide (0.293 mL, 4.70 mmol) was added and the resulting yellow solution was stirred at rt for 16 hr. The mixture was quenched with saturated NH4Cl aqueous solution, the volatiles were removed and the obtained residue was purified by silica gel column chromatography (elution with 0-50% EA/hexane) to give the title compound as a white solid (52.8 mg, 53% yield). LCMS: (FA) ES+ , 417/419. 1H NMR (300 MHz, DMSO) δ 7.37 (d, J=8.4 Hz, 2H), 7.13 (d, J=8.4 Hz, 2H), 6.75 (d, J=11.3 Hz, 1H), 4.36 (dt, J=30.3, 15.3 Hz, 1H), 3.59-3.34 (m, 2H), 3.03 (d, J=8.8 Hz, 3H), 2.38-2.15 (m, 1H), 2.12-1.92 (m, 1H).

Provenance & Evidence