Hydrochloric Acid → HCID 59807053, compound

Participants

Reaction Conditions

Reaction Steps

A suspension of Pd2(dba)3 (70 mg, 0.077 mmol) and PtBu3 10% wt in hexanes (0.94 m/L, 0.31 mmol) in THF (5.0 mL) was treated with a solution of compound 4 (500.0 mg, 1.55 mmol) in THF (5.0 mL) followed by LiHMDS 1 M in THF (3.1 mL, 3.1 mmol) at room temperature. The resulting brown mixture was stirred at 100° C. for 2 hours then cooled to room temperature and treated with 1 N HCl (10 mL) and stirred for 15 minutes. The mixture was basified with 1 N NaOH (25 mL) and extracted with CH2Cl2 (2×100 mL). The combined organic fractions were washed with brine (100 mL), dried (Na2SO4) and concentrated to give a dark brown residue. The crude product was purified by flash chromatography on silica gel (MeOH:CH2Cl2, 5:95 followed by 2 N NH3 in MeOH:CH2Cl2, 5:95) to give compound 5 (339.6 mg, 84.7%) as a dark viscous oil.

Provenance & Evidence