(Diethylamino)sulfur trifluoride → HCID 178490694, compound

Participants

Reaction Conditions

Reaction Steps

The product from Example 80 (50 mg, 0.12 mmol) in CH2Cl2 (4 mL) was treated with DAST (38 mg, 0.24 mmol) at −78° C. The mixture was stirred at −78° C. for 1.5 hrs, quenched with saturated aqueous NaHCO3 and extracted with CH2Cl2 (2×). The combined organic layers were dried over MgSO4, filtered and concentrated. The residue was purified by column chromatography using an Analogix® Intelliflash280™ (SiO2, 0-50% Hexane in ethyl acetate) to afford 29 mg (58%) of the title compound. 1H NMR (400 MHz, CDCl3) δ ppm 1.38 (d, J=21.48 Hz, 6H) 1.65 (s, 9H) 1.68-1.80 (m, 2H) 1.81-1.93 (m, 2H) 2.84 (t, J=7.67 Hz, 2H) 3.91 (s, 3H) 6.91 (d, J=8.90 Hz, 1H) 7.33 (dd, J=8.59, 2.76 Hz, 1H) 7.97 (s, 1H) 8.11 (d, J=2.76 Hz, 1H); MS (DCI/NH4+) m/z 427 (M+H)+.

Provenance & Evidence