HCID 60168011, compound → HCID 71678738, compound

Participants

Reaction Steps

To a solution containing 51 mg (0.15 mmol) of 2b in 4 mL of benzene was added 42 mg (0.46 mmol) of nickel peroxide. The reaction was stirred at reflux for 18 h. The reaction mixture was filtered through a silica gel plug and washed with three 20-mL portions of benzene, followed by two 20-mL portions of ethyl acetate. The combined organic layer was washed with brine, dried over anhydrous MgSO4, filtered, and concentrated under diminished pressure. The residue was purified via flash chromatography on a silica gel column (27×1.7 cm). Step gradient elution with 1:10→1:4 ethyl acetate-hexanes as eluent gave 6-decyl-1,4-dimethyl-1H-pyrrolo[2,3-b]pyridin-5-yl acetate (2e) as a colorless oil: yield 50 mg (48%); silica gel TLC Rf 0.35 (3:7 ethyl acetate-hexanes); 1H NMR (CDCl3) δ 1.05 (t, 3H, J=7.2 Hz), 1.39-1.52 (m, 14H), 1.76 (quint, 2H, J=8.0 Hz), 2.17 (s, 3H), 2.43 (s, 3H), 2.58 (t, 2H, J=8.0 Hz), 3.41 (s, 3H), 6.27 (d, 1H, J=3.6 Hz), 6.92 (d, 1H, J=3.6 Hz).

Provenance & Evidence