Diethyl Ether → HCID 86751468, compound

Participants

Reaction Steps

A suspension of 2-fluoro-5-methyl-11-chloroquindoline from Example 24 (300 mg, 0.35 mmol) in dry dioxane (30 mL) was added to a 1.0 M solution of C6H5MgBr in ether (6 mL, 6.0 mmol, obtained from Aldrich Chemical Co.) at room temperature. The reaction mixture was stirred for 1 hour at room temperature, then heated for 1 hour at 50° C. The reaction mixture was cooled, poured into ice-water (300 mL), allowed to stand overnight to effect hydrolysis (pH ~7), and then extracted with EtOAc (4×50 mL) and chloroform (4×50 mL). The combined chloroform and ethyl acetate extracts were washed with water, dried, concentrated, and then purified by chromatography on a basic alumina column, eluting 0.5-1.5% MeOH in CHCl3. The product containing fractions were combined, acidified with 1.0 M HCl solution in ether and concentrated to afford 175 mg (45.8%) of the title compound as a yellow solid, mp 251.4-251.8° C.; 1H NMR (DMSO-d6) δ 12.44 (s, NH), 9.00 (dd, J=4.4, J=9.2, 1H), 8.85 (d, J=8.4, 1H), 8.17 (t, J=7.6, 1H), 7.93 (t, J=7.8, 1H), 7.81-7.79 (m, 4H), 7.74-7.70 (m, 2H), 7.62 (d, J=9.2, 1H), 7.54 (t, J=7.2, 1H), 5.12 (s, 3H); 13C NMR (DMSO-d6) δ 159.66 (J=249.1), 146.35, 138.27, 136.45, 134.13, 132.80 (J=4.2), 131.15, 130.34, 129.94, 129.60, 129.39, 126.20 (J=9.9), 121.88 (J=9.1), 121.72, 121.66, 121.46, 114.01, 113.49, 109.94 (J=24.1), 49.94; (LSIMS, m/z) 327 (MH+).

Provenance & Evidence