Methyltriphenylphosphonium iodide → 6-Benzenesulfonyl-1-(4-methylene-cyclohexyl)-1,6-dihydro-1,2,3,5,6-pentaaza-as-indacene

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Reaction Steps

To a solution of Methyltriphenylphosphonium iodide (1.0 g, 2.5 mmol) in tetrahydrofuran (10 mL) was added slowly n-butyllithium (2.5 M in diethyl ether, 1 mL, 2.5 mmol) at −78° C., then the reaction mixture was stirred for 1 hour under nitrogen. To the reaction mixture was added 4-(6-Benzenesulfonyl-6H-1,2,3,5,6-pentaaza-as-indacen-1-yl)-cyclohexanone (400 mg, 1.01 mmol) slowly, then the reaction mixture was stirred for 3 hours under nitrogen and quenched with saturated aqueous ammonium chloride. The mixture was extracted with ethyl acetate. The organic phase was concentrated under reduce pressure to give 200 mg (76%) of 6-Benzenesulfonyl-1-(4-methylene-cyclohexyl)-1,6-dihydro-1,2,3,5,6-pentaaza-as-indacene. 1H NMR (400 MHz, DMSO-d6): δ: 9.18 (s, 1H), 8.15-8.12 (m, 3H), 7.72-7.68 (m, 1H), 7.63-7.59 (m, 2H), 7.44-7.43 (m, 1H), 5.22 (s, 1H), 4.76 (s, 2H), 2.49-2.41 (m, 4H), 2.26-2.23 (m, 2H), 2.05-2.02 (m, 2H).

Provenance & Evidence