1-Methyl-3-aminopyrazole → HCID 25261179, compound

Participants

Reaction Conditions

Reaction Steps

2-Bromo-5-propoxy-pyridine (0.96 mmol), sodium-tert.-butylate (1.4 eq.), and 1-methyl-1H-pyrazole-3-amine (1.3 eq.) are dissolved in degassed dioxane (2 ml) and heated to 80° C. Chloro-(di-2-norbornylphosphino)(2-dimethylaminoferrocene-1-yl)palladium (II) (5.9 mg) in degassed dioxane (1 ml) is added and the reaction mixture is heated for 60 min to 150° C. in the microwave. The reaction is quenched with ethylacetate/methanol (30 ml, 9:1) and filtrated over celite. The solvent of the filtrate is removed in vacuo. (1-Methyl-1H-pyrazole-3-yl)-(5-propoxy-pyridine-2-yl)-amine (“A23”) is obtained after reversed phase column chromatography (water/acetonitrile+0.1% TFA) as a colorless powder in a yield of 43%; HPLC (method C): 1.41 min; LC-MS (method A): 0.81 min, 233.0 (M+H+); 1H-NMR (DMSO-d6, 400 MHz): δ [ppm] 10.651 (s, 1H), 7.869 (d, 1H, J=2.9 Hz), 7.747-7.710 (m, 2H), 7.299 (d, 1H, J=9.6 Hz), 6.099 (d, 1H, J=2.3 Hz), 3.949 (t, 2H, J=6.4 Hz), 3.841 (s, 3H), 1.785-1.697 (m, 2H), 3.323 (t, 3H, J=7.4 Hz).

Provenance & Evidence