Nitrogen → (2S)-Methyl 2-(7-(4-allylchroman-6-yl)-2-(3-bromophenyl)-5-methylpyrazolo[1,5-a]pyrimidin-6-yl)-2-(tert-butoxy)acetate

Participants

Reaction Conditions

Reaction Steps

A solution of (S)-methyl 2-(2-(3-bromophenyl)-7-iodo-5-methylpyrazolo[1,5-a]pyrimidin-6-yl)-2-(tert-butoxy)acetate (0.375 g, 0.374 mmol), 2-(4-allylchroman-6-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (0.123 g, 0.411 mmol) and 2.0 M Na2CO3 (0.374 ml, 0.747 mmol) in DMF (3.74 ml) was sparged with N2 for 10 min, treated with Pd(Ph3P)4 (0.030 g, 0.026 mmol), sparged for 5 minutes, then heated (90° C.) for 16 h. The reaction was cooled, diluted with water (20 mL) and extracted with EtOAc. The organic layer was dried (MgSO4), filtered, and concentrated and the residue was purified by biotage (40 g SiO2, 0% (3 CV), 0-40% (15 CV), 60% (2 CV), EtOAc in hexanes). Fractions containing desired product combined, concentrated and re-purified (40 g SiO2, 0% (3 CV), 0-60% (15 CV), 60% (2 CV), EtOAc in hexanes) to afford the desired product (0.431 g, 0.713 mmol, 44.6% yield). LCMS (M+H)=606.4.

Provenance & Evidence