4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole → HCID 135900401, compound

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Reaction Steps

This compound may be prepared using methods as described for Compound 6, step 4 using [5-(5-bromo-[1,2,4]triazolo[1,5-a]pyrazin-8-ylamino)-2-morpholin-4-yl-phenyl]-methanol (85 mg, 0.21 mmol), 4-(4,4,5,5-tetramethyl-[1,3,2]dioxa-borolan-2-yl)-1H-pyrazole (81 mg, 0.42 mmol) and Pd(PPh3)4 (60 mg, 0.052 mmol) in 1.5M Na2CO3 (1.12 mL) and dioxane (2.0 mL). The reaction mixture is purified by silica gel column chromatography, eluting with 95:3 DCM:NH3 (7M in MeOH) followed by reverse phase preparative HPLC purification. The title compound is obtained as a pale brown solid (10 mg, 12%). 1H-NMR (400 MHz, d6-DMSO) δ (ppm) 2.87 (4H, m), 3.77 (4H, m), 4.63 (2H, d), 5.12 (1H, t), 7.11 (1H, d), 7.84 (1H, d), 8.12 (1H, s), 8.21 (1H, s), 8.39 (1H, s), 8.69 (1H, s), 8.77 (1H, s), 9.78 (1H, s), 13.29 (1H, br s). LCMS: Rt 2.45 min (96.3%), m/z (APCI) 393 (M+H)+.

Provenance & Evidence