Potassium Iodide → HCID 59004671, compound

Participants

Reaction Conditions

Reaction Steps

To a small reaction vial containing a magnetic stirbar was added compound 38 (155 mg, 0.649 mmol), potassium iodide (1.078 g, 6.49 mmol) and potassium carbonate (898.0 mg, 6.49 mmol). The vial was sealed and purged with argon. Anhydrous acetonitrile (4 mL) was added through the septum, followed by morpholine (0.57 mL, 6.54 mmol). The vial was placed in the heating block and stirred at 81° C. for 68 hours. The reaction was cooled to room temperature. The non-homogenous reaction was diluted with dichloromethane (5 mL) and filtered through celite. Additional dichloromethane (10 mL) followed by methanol (5 mL) was used to wash the celite plug. The filtrate was concentrated on the rotary evaporator and dried further under high vacuum. The product was purified using silica gel column chromatography (2M NH3 in methanol:CH2Cl2, 5:95) to obtain compound 39 (190 mg, 100%) as a yellow oil. 1H NMR (CDCl3) δ 8.59 (d, J=2.1 Hz, 1H), 8.11 (dd, J=2.7, 9.0 Hz, 1H), 7.42 (d, J=9.0 Hz, 1H), 7.28 (d, J=3.3 Hz, 1H), 6.69 (d, J=3.0 Hz, 1H), 4.30 (t, J=6.3 Hz, 2H), 3.75 (brs, 4H), 2.41 (brs, 4H), 2.27 (brs, 2H), 2.04 (brs, 2H); ESI-MS (m/z, %): 290 (M+1, 100).

Provenance & Evidence