Sodium Carbonate → HCID 68516875, compound

Participants

Reaction Conditions

Reaction Steps

A 100 mL round-bottomed flask was charged with 4-(1-(4-methoxybenzyl)-3-iodo-1H-pyrazolo[3,4-b]pyridin-4-yloxy)-3-fluorobenzenamine (250.0 mg, 0.5099 mmol, prepared in Example 7, step B), tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5,6-dihydropyridine-1(2H)-carboxylate (315.3 mg, 1.020 mmol), tetrakis(triphenylphosphine)palladium (117.8 mg, 0.1020 mmol), 1M Na2CO3 (1.275 ml, 2.550 mmol) and DME (25 mL). The reaction mixture was stirred at 100° C. overnight. The reaction was cooled to room temperature and partitioned between EtOAc and H2O. The phases were separated and the aqueous phase was re-extracted with EtOAc. The combined organic layers were dried (Na2SO4), filtered and concentrated to yield a crude product. The crude material was purified by silica gel chromatography (DCM/7 M NH3 in MeOH from 100/1 to 10/1, v/v) to afford product (273.3 mg, 98%). LRMS (APCI pos): >99% purity, 254 nm, m/e 546 (M+1).

Provenance & Evidence