6-Bromo-5-methyltetrazolo[1,5-a]pyridine → 5-methyl-6-(6-(trifluoromethyl)-1H-indazol-4-yl)tetrazolo[1,5-a]pyridine

Participants

Reaction Conditions

Reaction Steps

To a 20 mL microwave vial was added a mixture of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-6-(trifluoromethyl)-1H-indazole (50 mg, 0.160 mmol), 6-bromo-5-methyltetrazolo[1,5-a]pyridine (34.1 mg, 0.160 mmol), and PdCl2(dppf) (6.59 mg, 8.01 μmol) in dioxane (4 mL) and aqueous saturated NaHCO3 (2 mL). The resulting yellow suspension was heated at 130° C. for 30 minutes in a microwave reactor. The reaction mixture was subsequently purified by preparative HPLC, eluting with a gradient of 45-65% acetonitrile in H2O (containing 10 mM NH4HCO3). The product fractions were combined and dried to give the title compound. 1H NMR (400 MHz, CD3OD) δ ppm 2.83 (s, 3H), 7.51 (d, J=1.01 Hz, 1H), 7.91 (d, J=9.09 Hz, 1H), 8.04 (s, 1H), 8.06 (s, 1H), 8.10 (dd, J=9.09, 0.76 Hz, 1H); ESI-MS m/z [M+H]+ calc'd for C14H9F3N6, 319.1. found 319.3.

Provenance & Evidence