Potassium Iodide → 2-Methyl-1-[4-(3-pyrrolidin-1-ylpropoxy)phenyl]-1H-indole

Participants

Reaction Conditions

Reaction Steps

1-[4-(3-Chloropropoxy)phenyl]-2-methyl-1H-indole (20 mg, 0.067 mmol) was dissolved in N-methylpyrrolidinone (0.5 mL), and pyrrolidine (0.017 mL, 0.2 mmol), potassium carbonate (46 mg, 0.34 mmol), and a catalytic amount of potassium iodide were added. The reaction was heated to 70° C. overnight. The reaction was diluted with saturated sodium bicarbonate solution and extracted with ethyl acetate. The organic extracts were dried over MgSO4 and concentrated. The residue was purified by semi-prep LC-MS to give 9.6 mg of the desired product (43% yield). LC-MS (C22H26N2O calc'd 334) m/z 335 (M+H); 1H NMR (300 MHz, CDCl3) δ 7.58-7.53 (m, 1H), 7.26-7.25 (m, 3H), 7.12-6.99 (m, 4H), 6.37 (s, 1H), 4.10 (t, J=6 Hz, 2H), 2.99-2.90 (m, 6H), 2.24 (s, 3H), 2.22-2.14 (m, 2H), 2.00-1.90 (m, 6H).

Provenance & Evidence