Potassium Carbonate → HCID 16040141, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of 2-Fluorobenzyl bromide (47 μL, 0.377 mmol), 7-methyl-5-piperidin-4-ylmethyl-2-cyclohexylpropyl-2,3-dihydro-isoindol-1-one (75 mg, 0.251 mmol) and potassium carbonate (104 mg, 0.753 mmol) was added acetonitrile (3.0 mL). The mixture was stirred at 80° C. for 4 hours. 1 scoop of Sodium tert-butoxide (˜200 mg) was added and stirring continued overnight at 80° C. The mixture was cooled to room temperature, water (2.0 mL) was added and the product was extracted with ethyl acetate. The organic layer was washed with water, brine, dried over sodium sulfate, filtered and concentrated. Column chromatography provided the title compound as a yellow oil (6.6 mg, 6%). 1H NMR (300 MHz, CDCl3): δ 7.38 (m, 1H), 7.23-7.13 (m, 1H), 7.11-7.00 (m, 3H), 6.96 (s, 1H), 4.41 (s, 2H), 3.61 (s, 2H), 3.46-3.44 (d, 2H), 2.95-2.92 (d, 2H), 2.70 (s, 3H), 2.59-2.57 (d, 2H), 2.01-1.98 (t, 2H), 1.65-1.61 (m, 3H), 1.38-1.27 (m, 2H), 1.04 (m, 1H), 0.60-0.55 (m, 2H), 0.36-0.32 (m, 2H).

Provenance & Evidence