Reaction Steps
A mixture of 12-bromo-4-[1-(oxolan-3-yl)-1H-1,2,4-triazol-5-yl]-9-oxa-3,6-diazatricyclo[8.4.0.02,6]tetradeca1(14),2,4,10,12-pentaene (40 mg, 0.010 mmol), 1-methyl-4-(pyrrolidin-2-yl)piperidine (3.0 mg, 0.020 mmol), Pd(PtBu3)2 (1.0 mg, 0.0010 mmol), NaOtBu (2.9 mg, 0.030 mmol) in toluene (2.0 ml) in a seal tube was degassed with N2 for three times. The resulting mixture was stirred at 110° C. for 1 h. The solid was filtered off and the filtrate was concentrated to give the crude product, which was purified by prep-HPLC (Gilson GX 281, Shim-pack PRC-ODS 250 mm×20 mm×2, gradient: CH3CN/1% formic acid, 17 min) to afford 232 (8.0 mg, 16% yield). LCMS (ESI): RT=3.39 min, m/z: 490.2 [M+H+]. 1H NMR (500 MHz, DMSO-d6) δ 8.40 (s, 1H), 7.31 (s, 1H), 8.02 (s, 1H), 7.93 (s, 1H), 6.60 (d, J=9 Hz, 1H), 6.42 (d, J=2.5 Hz, 1H), 4.54-4.52 (m, 4H), 4.29 (q, J=16 Hz, 1H), 4.16 (q, J=23 Hz, 1H), 4.03-4.01 (m, 1H), 3.97-3.95 (m, 1H), 3.86 (s, 1H), 3.55-3.53 (m, 1H), 3.24 (d, J=8 Hz, 1H), 2.98 (t, J=21 Hz, 2H), 2.56-2.48 (m, 2H), 2.29 (d, J=12 Hz, 3H), 2.04-1.93 (m, 5H), 1.78 (s, 1H), 1.69 (d, J=11.5 Hz, 1H), 1.53-1.44 (m, 3H)
