Chloroform → HCID 67598117, compound

Participants

Reaction Conditions

Reaction Steps

A suspension of quindoline (1 g, 4.58 mmol) from Example 2, benzyl bromide (3 mL, 25.1 mmol) and dry chloroform (5 mL) was heated in a bomb at 140° C. for 48 hours. A solution of aqueous 5% Na2CO3 (100 mL) was added and the reaction mixture was extracted with chloroform (2×250 mL). The extract was evaporated to dryness. The residue was purified on a basic alumina column eluting with 1-2% MeOH in CHCl3, and the combined fractions were acidified with a solution of 1.0 M HCl in ether and concentrated to afford 0.65 g (32.7%) of the title compound as an orange solid, mp 244.4-244.7° C.; 1H NMR (DMSO-d6) δ 9.87 (s, 1H), 8.59 (d, J=8.0, 1H), 8.55 (d, J=9.2, 1H), 8.37 (d, J=8.4, 1H), 8.04-7.93 (m, 3H), 7.45 (t, J=7.2, 1H), 7.40-7.28 (m, 10 H), 6.87 (s, 2H), 6.06 (s, 2H); 13C NMR (DMSO-d6) δ 145.84, 138.05, 136.03, 135.36, 134.74, 134.46, 133.29, 133.14, 130.13, 129.19, 128.81, 128.18, 127.84, 127.65, 126.95, 126.49, 126.08, 125.63, 125.13, 122.13, 117.78, 113.11, 111.99,55.17, 46.28; MS (LSIMS, m/z) 399 (MH+).

Provenance & Evidence