Butyl bromide → HCID 178448422, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of the product from Example 26B (mixture) in 10 mL of N,N-dimethylformamide and tetrahydrofuran (1:4) were added potassium t-butoxide (21 mg, 0.18 mmol) and 1-bromobutane (25 mg, 0.18 mmol). After stirring at 80° C. for 16 h, the reaction mixture was cooled to room temperature and quenched with saturated aqueous NaHCO3 (10 mL). The aqueous layer was extracted with ethyl acetate (3×20 mL). The combined organic extracts were dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by column chromatography using an Analogix® Intelliflash280 ™ (SiO2, 0-50% ethyl acetate in methylene chloride) to afford 3 mg of the title compound as a single regioisomer. 1H NMR (300 MHz, DMSO-d6) δ ppm 0.94 (t, J=7.3 Hz, 3H), 1.28-1.42 (m, 2H), 1.73 (t, 2H), 2.06 (t, 2H), 2.67 (t, J=6.3 Hz, 2H), 3.79 (s, 3H), 4.06-4.13 (m, 2H), 4.18-4.25 (m, 2H), 7.11 (d, J=8.8 Hz, 1H), 7.45 (dd, J=8.8, 3.1 Hz, 1H), 7.71 (d, J=3.1 Hz, 1H); MS (ESI+) m/z 381 (M+H)+.

Provenance & Evidence