HCID 178418348, compound → HCID 178448418, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of methyllithium (0.8 mL, 1.3 mmol, 1.6M in tetrahydrofuran, Aldrich) in tetrahydrofuran (10 mL) was added slowly a solution of Example 10 (0.25 g, 0.63 mmol) in tetrahydrofuran (5 mL) at −78° C. The reaction mixture was stirred at −78° C. for 30 minutes and was allowed to reach room temperature. The reaction mixture was quenched with water (10 mL) and extracted with EtOAc (2×20 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, 0-5% methanol in methylene chloride) to afford 92 mg (35%) of the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 0.93 (t, J=7.3 Hz, 3H), 1.24-1.37 (m, 2H), 1.39 (s, 3H), 1.56-1.76 (m, 2H), 3.64-3.70 (m, J=3.4 Hz, 2H), 3.79 (s, 3H), 3.92-4.13 (m, 2H), 4.55-4.80 (m, 2H), 5.57 (s, 1H), 7.12 (d, J=9.2 Hz, 1H), 7.46 (dd, J=9.0, 2.9 Hz, 1H), 7.73 (s, 1H)); MS (ESI+) m/z 411 (M+H)+.

Provenance & Evidence