Cesium fluoride → HCID 68513319, compound

Participants

Reaction Conditions

Reaction Steps

A 50 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 (40.0 mg, 0.0566 mmol, prepared in Example 63, step A), tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole-1-carboxylate (50.0 mg, 0.170 mmol), Pd(OAc)2 (2.54 mg, 0.0113 mmol), tricyclohexylphosphine (4.76 mg, 0.0170 mmol), cesium fluoride (77.4 mg, 0.510 mmol) and CH3CN (10 mL). The reaction mixture was stirred at 100° C. for 1 hour. The reaction was cooled to room temperature and then the reaction was 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 (29.7 mg, 70.2%). LRMS (APCI neg): >96% purity, 254 nm, m/e 745 (M−1).

Provenance & Evidence