1-Bromo-2-methylpropane → HCID 178490655, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of Example 3F (1.0 g, 2.8 mmol) in N,N-dimethylformamide/tetrahydrofuran (1:4, 20 mL) was added potassium tert-butoxide (0.35 g, 3.1 mmol, Aldrich), 1-bromo-2-methylpropane (0.43 g, 3.1 mmol, Aldrich) and tetrabutyl ammonium iodide (0.1 g, 0.3 mmol, Aldrich). After stirring at 80° C. for 16 h, the reaction mixture was cooled to room temperature and quenched with saturated aqueous NaHCO3 (20 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, 0-100% ethyl acetate in hexanes) to afford 90 mg (29%) of the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 0.81-0.88 (m, 3H), 0.91 (s, 3H), 1.46 (s, 6H), 2.29 (t, 1H), 2.67 (t, J=5.4 Hz, 2H), 3.79 (s, 3H), 3.88-4.11 (m, 4H), 7.12 (d, J=9.1 Hz, 1H), 7.46 (dd, J=8.7, 2.8 Hz, 1H), 7.67 (d, J=3.2 Hz, 1H); MS (ESI+) m/z 409 (M+H)+; Anal. Calculated CO1H25ClN3O3S: C, 58.74; H, 60.16; N, 6.85. Found: C, 58.80; H, 5.97; N, 6.88.

Provenance & Evidence