A solution of (S)-methyl 2-(2-(3-bromophenyl)-7-iodo-5-methylpyrazolo[1,5-a]pyrimidin-6-yl)-2-(tert-butoxy)acetate (0.100 g, 0.179 mmol), 4-allyl-7-methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,4-dihydro-2H-benzo[b][1,4]oxazine (0.062 g, 0.197 mmol) and 2.0 M Na2CO3 (0.179 mL, 0.358 mmol) in dry DMF (3 mL) was sparged with N2 for 10 min, treated with Pd(Ph3P)4 (0.014 g, 0.013 mmol), sparged for 5 minutes, then heated (90° C.) for 48 h. The reaction was cooled, filtered (0.45 μm syringe tip filter) and purified by prep-HPLC to afford the desired product (0.028 g, 0.045 mmol, 25.2% yield) as a yellow oily film. 1H NMR (500 MHz, CDCl3) δ 7.99 (t, J=1.7 Hz, 1H), 7.78 (dt, J=7.7, 1.3 Hz, 1H), 7.49-7.42 (m, 1H), 7.26-7.22 (m, 1H), 6.87-6.80 (m, 2H), 6.61 (s, 1H), 5.86-5.73 (m, 1H), 5.22 (dd, J=17.2, 1.6 Hz, 1H), 5.17 (dd, J=10.2, 1.4 Hz, 1H), 5.11 (s, 1H), 4.42-4.30 (m, 2H), 3.87-3.78 (m, 1H), 3.75-3.68 (m, 1H), 3.66 (s, 3H), 3.42-3.34 (m, 1H), 3.32-3.24 (m, 1H), 2.76 (s, 3H), 1.90 (s, 3H), 1.17 (s, 9H). LCMS (M+H)=621.3.
