Methyl iodide → HCID 86751473, compound

Participants

Reaction Conditions

Reaction Steps

In a large teflon lined steel bomb fitted with a stir bar was placed 7-bromo-8-chloroquindoline from Example 75 (0.350 g, 1.06 mmol) and methyl iodide (1.97 mL, 31.7 mmol). The bomb was flushed with nitrogen, sealed, and heated to 150° C. for 24 h. The bomb was cooled, opened and the contents were transferred to a flask using chloroform to wash the inside of the bomb. The chloroform suspension was concentrated to a dry orange residue. The orange residue was suspended in chloroform, adsorbed onto Na2CO3 and chromatographed over basic alumina using 100% chloroform until starting material could not be detected by TLC. The column was eluted with 2% methanol in chloroform and the violet fractions were collected. After concentrating to a small volume (~50 mL) the violet solution was acidified with ethereal 1 M HCl to a bright yellow endpoint. The mixture was cooled below room temperature, filtered and dried under high vacuum at 45° C. for several days to yield 0.311 (77%) of the title compound as a bright orange solid, mp >246° C.; 1H NMR (DMSO-d6) δ 13.33 (s, 1H), 9.38 (s, 1H), 9.21 (s, 1H), 8.82 (d, J=8.8, 1H), 8.60 (d, J=8.0, 1H), 8.17-8.35 (m, 2H), 7.98 (t, J=7.6, 1 H), 5.02 (s, 3H); 13C NMR (DMSO-d6) δ 144.42, 137.91, 136.67, 135.73, 133.85, 133.09, 130.27, 130.00, 127.53, 126.76, 126.08, 118.02, 114.48, 114.36, 113.63, 40.46; MS (LSIMS, m/z) 347 (M+2+).

Provenance & Evidence