Cyclopropylboronic acid → HCID 178439237, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of ethyl (trans-4-{[[2-({(4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-4-methyl-2-oxo-1,3-oxazolidin-3-yl}methyl)-6-chloropyridin-3-yl](ethyl)amino]methyl}cyclohexyl)acetate, cyclopropylboronic acid and 1,1′-bis(di-t-butylphosphinoferrocene) palladium dichloride in 1N aqueous potassium carbonate and THF was heated at 85° C. in a sealed tube overnight. The reaction was diluted with water (10 mL) and extracted with EtOAc (3×20 mL). The combined extracts were dried (Na2SO4) and concentrated in vacuo to give the crude product. This was purified by flash chromatography (Si, 12×160 mm, 0-30% EtOAc in hexanes gradient) to afford ethyl (trans-4-{[[2-({(4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-4-methyl-2-oxo-1,3-oxazolidin-3-yl}methyl)-6-isopropenylpyridin-3-yl](ethyl)amino]methyl}cyclohexyl)acetate. Rf=0.44 (20% EtOAc/hexanes). LCMS calc.=670.3; found=670.4 (M+1)+. 1H NMR (600 MHz, CDCl3): δ 7.87 (s, 1 H); 7.78 (s, 2 H); 7.40 (s, 2 H); 5.85 (s, 1 H); 5.75 (d, J=8.6 Hz, 1 H); 5.25 (s, 1 H); 4.96 (d, J=16.7 Hz, 1 H); 4.42-4.36 (m, 2 H); 4.08 (q, J=7.1 Hz, 2 H); 2.98-2.92 (m, 2 H); 2.85 (dd, J=6.5, 13.0 Hz, 1 H); 2.76 (dd, J=7.5, 13.0 Hz, 1H); 2.20 (s, 3 H); 2.12 (d, J=6.8 Hz, 2 H); 1.83-1.65 (m, 5 H); 1.36-1.30 (m, 1 H); 1.22 (t, J=7.1 Hz, 3 H); 0.99 (t, J=7.0 Hz, 3 H); 0.95-0.83 (m, 4 H); 0.72 (d, J=6.7 Hz, 3 H).

Provenance & Evidence