Hydrochloric Acid → HCID 59807098, compound

Participants

Reaction Conditions

Reaction Steps

A suspension of Pd2(dba)3 (105 mg, 0.11 mmol) and PtBu3 (10% wt in hexanes, 1.40 mL, 0.46 mmol) in anhydrous THF (5 mL) was treated with a solution of compound 5 (713 mg, 2.30 mmol) in THF (10 mL) followed by LiHMDS (1 M in THF, 4.6 mL, 4.60 mmol) at room temperature. The resulting dark brown mixture was heated to 100° C. and stirred for 3 hours in a sealed tube. The reaction mixture was cooled to room temperature and treated with 1 N HCl (20 mL) and stirred for 15 min, then basified with 1 N NaOH (50 mL). The product was extracted into CH2Cl2 (2×50 mL) and the combined organic fractions were washed with brine (25 mL), dried (MgSO4), filtered and concentrated to give a dark brown residue. The crude product was purified by column chromatography (2 N NH3 in MeOH:CH2Cl2, 5:95) to give compound 6 (531 mg, 94%) as a syrup.

Provenance & Evidence