HCID 71678736, compound → HCID 71678737, compound

Participants

Reaction Steps

To a solution containing 65 mg (0.20 mmol) of 1d in 5 mL of benzene was added 56 mg (0.61 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 25-mL portions of benzene, followed by two 25-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 (25×1.7 cm). Step gradient elution with 1:10→1:4 ethyl acetate-hexanes as eluent gave 1,4-dimethyl-6-octyl-1H-pyrrolo[2,3-b]pyridin-5-yl acetate (2d) as a colorless oil: yield 50 mg (48%); silica gel TLC Rf 0.29 (3:7 ethyl acetate-hexanes); 1H NMR (CDCl3) δ 0.98 (t, 3H, J=7.2 Hz), 1.35-1.50 (m, 10H), 1.72 (quint, 2H, J=8.0 Hz), 2.11 (s, 3H), 2.38 (s, 3H), 2.52 (t, 2H, J=8.0 Hz), 3.34 (s, 3H), 6.21 (d, 1H, J=3.6 Hz), 6.88 (d, 1H, J=3.6 Hz).

Provenance & Evidence