Ammonia → 7'-Bromo-5''-methyl-3',4'-dihydrodispiro[cyclopropane-1,2'-naphthalene-1',2''-imidazol]-4''-amine

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Reaction Steps

7′-Bromo-5″-methyl-3′,4′-dihydrodispiro[cyclopropane-1,2′-naphthalene-1′,2″-imidazole]-4″(3″H)-thione (Intermediate 12, 0.688 g, 2.05 mmol) in ammonia (7 M in methanol, 18 mL, 126 mmol) was heated in a microwave reactor for 60 min at 100° C. Five times the mixture was concentrated, re-dissolved in ammonia (7 M in methanol, 18 mL, 126 mmol) and microwaved again for 40 to 60 minutes at 100° C. Purification by flash silica gel chromatography using a stepwise gradient of CHCl3/MeOH (30:1-20:1-10:1) gave the title compound (0.532 g, 81% yield). 1H NMR (500 MHz, DMSO-d6) δ ppm 0.00-0.08 (m, 1 H), 0.11 (ddd, 1 H), 0.22 (ddd, 1 H), 0.51 (dt, 1 H), 1.46 (dt, 1 H), 2.17 (s, 3 H), 2.28-2.39 (m, 1 H), 2.82-2.98 (m, 2 H), 6.56 (d, 1 H), 6.58 (br. s., 2 H), 7.12 (d, 1 H), 7.30 (dd, 1 H); MS (ES+) m/z 318.0 [M+H]+.

Provenance & Evidence