5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)isoindolin-1-one → 5-(8-(4-Morpholinophenylamino)-[1,2,4]triazolo[1,5-a]pyrazin-5-yl)isoindolin-1-one

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Reaction Steps

This compound may be prepared using methods as described for Compound 6, step 4 using (5-bromo-[1,2,4]triazolo[1,5-a]pyrazin-8-yl)-(4-morpholin-4-yl-phenyl)-amine (1.0 g, 2.67 mmol), 5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-2,3-dihydro-isoindol-1-one (see description for Compound 79) (1.03 g, 4.01 mmol) and Pd(PPh3)4 (0.77 g, 0.67 mmol) in 1.5M Na2CO3 (14.3 mL) and dioxane (40 mL). Purification by silica gel column chromatography eluting with DCM followed by 96:4 DCM:NH3 (7M in MeOH) affords the title compound (0.895 g, 79%). 1H-NMR (400 MHz, d6-DMSO) δ(ppm) 3.12 (4H, m), 3.79 (4H, m), 4.51 (2H, s), 7.01 (2H, d), 7.84 (1H, d), 7.92 (2H, d), 8.01 (1H, s), 8.09 (1H, d), 8.23 (1H, s), 8.72 (1H, s), 8.73 (1H, s), 10.02 (1H, s). LCMS: Rt 2.51 min (97.8%), m/z (APCI) 428 (M+H)+.

Provenance & Evidence