Sodium Carbonate → HCID 57666539, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-bromo-6-(2,2,6,6-tetramethyl-tetrahydro-pyran-4-yl)-pyridin-3-ylamine (as prepared in the previous step, 17.0 g, 0.054 mol ) in DME (200 mL) was added 2 M aq Na2CO3 (214 mL, 0.428 mol), LiCl (2.70 g, 0.0600 mol ) and 2-(4,4-dimethyl-cyclohex-1-enyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane (15.3 g, 0.064 mol). The resulting mixture was degassed by sonication under Ar and Pd(PPh3)4 (6.20 g, 5.30 mmol) was added and the reaction heated at 80° C. under Ar overnight. The reaction mixture was allowed to cool to RT and was extracted with EtOAc. After concentrating, the resulting residue was purified on silica gel with 2-20% EtOAc:hexane to give the title compound as a white solid (14.8 g, 80%). Mass spectrum (ESI, m/z): Calcd. for C22H34N2O, 343.2 (M+H), found 343.3.

Provenance & Evidence