Stannane → 3-(Furan-2-yl)-7-(5-methylisoxazol-3-yl)-2-(1-methyl-1H-[1,2,4]triazol-5-ylmethoxy)pyrazolo[1,5-d][1,2,4]triazine

Participants

Reaction Steps

A stirred mixture of 3-bromo-7-(5-methylisoxazol-3-yl)-2-(1-methyl-1H-[1,2,4]triazol-5-ylmethoxy)pyrazolo[1,5-d][1,2,4]triazine (Example 7) (80 mg, 0.20 mmol) in dioxan (10 mL) containing 2-tri-n-butylstannylfuran (146 mg, 0.41 mmol) was degassed with nitrogen for 20 min. Tetrakis-triphenylphosphine palladium(0) (50 mg) and copper(I)iodide (5 mg) were added and the mixture heated at reflux for 8 h. Further stannane (146 mg, 0.41 mmol) and palladium catalyst (50 mg) were added and the mixture heated at reflux for 16 h. The solvent was evaporated and the residue purified on silica eluting with 5% MeOH/DCM to give a yellow solid (149 mg). The yellow solid was re-chromatographed on silica eluting with 5% MeOH/DCM to give a yellow solid (29 mg) which was triturated with diethylether to give the title compound (15 mg, 19%) as a yellow solid. mp 226-228° C. 1H NMR (360 MHz, CDCl3) δ1.58 (9H, s), 2.61 (3H, s), 4.10 (3H, s), 5.78 (2H, s), 6.52-6.56 (1H, m), 6.75-6.79 (1H, m), 6.96 (1H, s), 7.57 (1H, s), 7.91 (1H, s), 9.71 (1H, s). Found: C, 52.68; h, 3.47; N, 28.64; C17H14N8O3.0.05(CH2Cl2).0.25(H2O) requires: C, 52.90; H, 28.95%.

Provenance & Evidence