Sodium Carbonate → HCID 178481035, compound

Participants

Reaction Steps

Dissolve 3-(4-Bromo-2-chloro-benzyl)-1-(4,5,6,7-tetrahydro-2H-indazol-5-yl)-pyrrolidin-2-one (Example 6) (0.471, 1.16 mmol) in DME (5.0 mL) and de-gas with a stream of nitrogen for 5.0 minutes. Add (4-Methyl-piperazin-1-yl)-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-methanone hydrochloride (0.1.14 g, 1.58 mmol), followed by 2.0 M sodium carbonate (2.03 mL, 4.06 mmol) and continue de-gas. Add Pd(Ph3)4 (0.134 g, 0.116 mmol) and heat to 80° C. for 17 hours. Dilute with ethyl acetate and water, separate and save both layers. The pH of the aqueous layer adjusted to ph 9 with 1.0 N HCl, and back extract with three portions of ethyl acetate. The organic layers are combined, dry over sodium sulfate and evaporate. Chromatography (silica 95:5 CH2Cl2/MeOH/1% NH3) yields 0.08 g (0.6%) of the title compound as an amorphorous foam. MS (m/z): 533 (M+1).

Provenance & Evidence