Water → HCID 67100256, compound

Participants

Reaction Conditions

Reaction Steps

To 1,1-dimethylethyl N-((4′-hydroxy-2′-oxo-6′-chloro-spiro[cyclopentane-1,1′-naphthalen]-3′-yl)carbonyl)glycinate (250 mg, 616 μmol, Example 25A-B) and phenylboronic acid (113 mg, 924 μmol) were added 1,4-dioxane (3080 μL) and K2CO3 in water (924 μL, 1848 μmol). The reaction was then flushed with nitrogen for 10 minutes. Pd2(dba)3 (56.4 mg, 61.6 μmol) and X-Phos (58.7 mg, 123 μmol) were then added, and the reaction mixture was stirred at 110° C. for 6 hours. The reaction mixture was diluted with 75 mL of EtOAc, added to a separatory funnel, partitioned with NaHCO3 (saturated, aqueous), washed 2 times with 50 mL of NaHCO3 (saturated, aqueous), separated, dried over Na2SO4, and concentrated in vacuo to give the title compound (115 mg) as an oil after preparatory LC. MS (m/z)=392 (M+H-tBu)+.

Provenance & Evidence