Water → HCID 67099935, compound

Participants

Reaction Conditions

Reaction Steps

To 1,1-dimethylethyl N-((6-chloro-4-hydroxy-1,1-dimethyl-2-oxo-naphthalen-3-yl)carbonyl)glycinate (250 mg, 658 μmol, Example 40A-D) and o-tolylboronic acid (134 mg, 987 μmol), were added 1,4-dioxane (3291 μL), and K2CO3 in water (987 μL, 1975 mmol). The reaction was flushed with nitrogen for 10 minutes. Next, Pd2(dba)3 (60.3 mg, 65.8 μmol) and X-Phos (62.8 mg, 132 μmol) were added, and the reaction was heated at 110° C. for 4 hours. The reaction mixture was then diluted with 100 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 (160 mg) as a yellow oil. MS (m/z)=380(M+H-tBu)+.

Provenance & Evidence