Sodium Iodide → N-[(4,6-dimethyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]-1-(1-methylethyl)-6-(4-pyridinylethynyl)-1H-pyrazolo[3,4-b]pyridine-4-carboxamide

Participants

Reaction Steps

The title compound was prepared in the same manner as described in example 31 from 6-chloro-N-[(4,6-dimethyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]-1-(1-methylethyl)-1H-pyrazolo[3,4-b]pyridine-4-carboxamide (0.15 g, 0.401 mmol), sodium iodide (0.012 g, 0.080 mmol), zinc (5.25 mg, 0.080 mmol), DMSO (4.0 mL), triethylamine (0.168 mL, 1.204 mmol), DBU (0.121 mL, 0.802), 4-ethynylpyridine (0.112 g, 0.802 mmol), and Pd(Ph3P)4 (0.046 g, 0.040 mmol). The crude product was purified by silica gel chromatography (eluent: Gradient of 5-100% of DCM and chloroform containing 10% 2M Ammonia (in methanol)). The isolated product was dried in vacuum oven for 18 hr. to afford the final product as 0.032 g (18%). LCMS E-S (M+H)=441.1. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.51 (d, J=6.57 Hz, 6H), 2.13 (s, 3H), 2.21 (s, 3H), 4.37 (d, J=4.80 Hz, 2H), 5.20-5.32 (m, 1H), 5.90 (s, 1H), 7.62-7.69 (m, 2H), 7.93 (s, 1H), 8.45 (s, 1H), 8.67-8.75 (m, 2H), 8.93 (t, J=4.80 Hz, 1H), 11.55 (s, 1H).

Provenance & Evidence