Cesium fluoride → HCID 68512288, compound

Participants

Reaction Conditions

Reaction Steps

A 100 mL round-bottomed flask was charged with N-(4-(1-(4-methoxybenzyl)-3-iodo-1H-pyrazolo[3,4-b]pyridin-4-yloxy)-3-fluorophenyl)-2-(4-fluorophenyl)-3-oxo-2,3-dihydropyridazine-4-carboxamide (50.0 mg, 0.0708 mmol, prepared in Example 63, step A), 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (44.2 mg, 0.212 mmol), Pd(OAc)2 (3.18 mg, 0.0142 mmol), tricyclohexylphosphine (5.95 mg, 0.0212 mmol), cesium fluoride (96.8 mg, 0.637 mmol) and CH3CN (10 mL). The reaction mixture was stirred at 100° C. 1 hour. 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 (23.8 mg, 50.9%). LRMS (APCI pos): >95% purity, 254 nm, m/e 661 (M+1).

Provenance & Evidence