4-Aminopyridine → HCID 58404912, compound

Participants

Reaction Conditions

Reaction Steps

3-bromo-4-methoxy-6-(1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyridine (30 mg, 0.098 mmol), 4-aminopyridine (18 mg, 0.20 mmol), 1,8-diazabicyclo[5.4.0]undec-7-ene (0.059 ml, 0.39 mmol), molybdenum hexacarbonyl (0.013 ml, 0.098 mmol), tri-(tert-butyl)phosphonium hydrogen tetrafluoroborate salt (3.0 mg, 0.01 mmol), trans-di-mu-acetatobis[2-(di-o-tolylphosphino)benzyl]dipalladium (II) (4.6 mg, 0.0049 mmol) were added to dioxane (3.9 ml). The mixture was sparged with argon for 3 minutes and heated to 100° C. After 16 h, the reaction mixture was cooled and purified directly by preparative HPLC Reverse phase (C-18), eluting with acetonitrile/water+0.05% TFA to give 4-methoxy-6-(1-methyl-1H-pyrazol-4-yl)-N-pyridin-4-ylpyrazolo[1,5-a]pyridine-3-carboxamide. 1H NMR (500 MHz, DMSO-d6) δ 10.30 (s, 1H); 8.81 (s, 1H); 8.44 (d, 2H); 8.37 (d, 2H); 8.09 (s, 1H); 7.67 (d, 2H); 7.24 (s, 1H); 4.10 (s, 3H); 3.88 (s, 3H). LRMS (ESI) calculated for C18H17N6O2 [M+H]+, 349.1 found 349.0.

Provenance & Evidence