Water → 6-{4-[(Dimethylamino)sulfonyl]phenyl}-N-[(4,6-dimethyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]-1-(1-methylethyl)-1H-pyrazolo[3,4-b]pyridine-4-carboxamide

Participants

Reaction Conditions

Reaction Steps

In a 25 mL sealable tube under nitrogen were combined 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 (85 mg, 0.23 mmol) and {4-[(dimethylamino)sulfonyl]phenyl}boronic acid (104 mg, 0.46 mmol) in DME/water (3 ml:1 ml). PdCl2(dppf)-CH2Cl2 adduct (9.3 mg, 0.011 mmol) was added and the resulting mixture was degassed with nitrogen for 10 min. Sodium bicarbonate (57.3 mg, 0.68 mmol) was added and the insoluble light brown mixture was heated in an oil bath at 110° C. for 3 hrs. After cooling, 2 mL of water was added to the black mixture and solids that precipitated were filtered. DMF was added along with a few drops of water and solids were filtered. DCM/MeOH (1:1) was added to the grey solids and they were filtered and dried to afford the title compound (69 mg, 57%) as a grayish solid. LCMS E-S (M+H)=523.2. 1H NMR (400 MHz, DMSO-d6) δ ppm 11.59 (br. s., 1H), 9.01 (br. s., 1H), 8.51 (m, J=8.34 Hz, 2H), 8.44 (s, 1H), 8.27 (s, 1H), 7.93 (m, J=8.34 Hz, 2H), 5.91 (s, 1H), 5.36 (dt, J=13.14, 6.57 Hz, 1H), 4.43 (d, J=4.55 Hz, 2H), 2.66 (s, 6H), 2.23 (s, 3H), 2.13 (s, 3H), 1.56 (d, J=6.57 Hz, 6H).

Provenance & Evidence