Sodium hydride → HCID 178448630, compound

Participants

Reaction Steps

The product from Example 21A (91 mg, 1.01 mmol) in THF (2 mL) was treated with NaH (60%) (40.3 mg, 1.01 mmol) at room temperature for 20 minutes. To the above mixture was added the product from Example 20B (200 mg, 0.5 mmol) in THF (2 mL). After 4 hrs, the reaction mixture was quenched with saturated aqueous NaHCO3 (20 mL) and extracted with ethyl acetate. 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 82.4 mg (35%) of the title compound. 1H NMR (500 MHz, CDCl3) δ ppm 1.04 (t, J=7.63 Hz, 3H) 1.38 (s, 6H) 1.48-1.55 (m, 2H) 1.89-1.97 (m, 2H) 4.03 (s, 2H) 4.54 (t, J=7.32 Hz, 2H) 4.62 (brs, 1H) 7.08 (d, J=8.85 Hz, 1H) 7.66 (d, J=4.58 Hz, 1H) 7.70 (dd, J=8.54, 2.14 Hz, 1H) 8.51 (d, J=5.19 Hz, 1H) 8.51 (s, 1H) 8.74 (s, 1H); MS (ESI+) m/z 468 (M+H)+.

Provenance & Evidence