Potassium Carbonate → HCID 66745204, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of tert-butyl N-[5-bromo-3-[5-[4-(bromomethyl)phenyl]-1,3,4-oxadiazol-2-yl]pyrazin-2-yl]-N-tert-butoxycarbonyl-carbamate (500 mg, 0.82 mmol) in toluene (4.4 mL)/water (484 μL) was added tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,6-dihydro-2H-pyridine-1-carboxylate (304 mg, 1.0 mmol) followed by the addition of 4-ditert-butylphosphanyl-N,N-dimethyl-aniline; dichloropalladium (58 mg, 0.082 mmol) and K2CO3 (226 mg, 1.6 mmol). The reaction mixture was heated at 60° C. for 3 h. The reaction mixture was partitioned between DCM and saturated aqueous NaHCO3, the layers were separated and the aqueous layer was extracted with DCM. The combined organics were dried over Na2SO4, filtered and concentrated to brown oil. The crude material was purified by silica gel column chromatography using 0-20% EtOAc in hexanes to yield tert-butyl 4-[5-[bis(tert-butoxycarbonyl)amino]-6-[5-[4-(bromomethyl)phenyl]-1,3,4-oxadiazol-2-yl]pyrazin-2-yl]-3,6-dihydro-2H-pyridine-1-carboxylate (350 mg, 60%). 1HNMR (400 MHz, CDCl3) δ 8.74 (s, 1H), 8.22 (d, J=33.8 Hz, 2H), 7.59 (d, J=8.2 Hz, 2H), 6.92 (s, 1H), 4.54 (s, 2H), 4.24 (s, 2H), 3.73 (t, J=5.5 Hz, 2H), 2.79 (d, J=0.8 Hz, 2H), 1.37 (s, 18H), 1.24 (s, 9H).

Provenance & Evidence