Sodium Bicarbonate → HCID 58504704, compound

Participants

Reaction Steps

(4-Cyano-3-fluorophenyl)boronic acid (0.261 g, 1.582 mmol) was added to a 20 mL microwave vessel followed by the addition of Pd(PPh3)4 (0.046 g, 0.040 mmol) and (2S,5R)-4-[6-chloro-2-(methylamino)-4-pyrimidinyl]-N-cyclohexyl-5-ethyl-2-morpholinecarboxamide (0.302 g, 0.791 mmol) dissolved in 1,4-dioxane (5 mL). Saturated aqueous NaHCO3 (2.5 mL) was added and the reaction was irradiated at 130° C. for 30 minutes. SiliaBond® Thiol (3.04 g, 3.96 mmol) was added to the reaction and it was stirred at room temperature for 2 hours and then filtered. The filtrate was then diluted with H2O and extracted with EtOAc (2×). The organics were dried and concentrated to afford the crude title compound (0.387 g) as a dark brown oil. LC-MS (ES) m/z=467 [M+H]+.

Provenance & Evidence