Pyridine → 1-(3-(6-tert-butyl-8-fluoro-1-oxophthalazin-2(1H)-yl)-2-(hydroxymethyl)phenyl)-6-vinyl-1H-pyrrolo[2,3-b]pyridine-3-carbonitrile

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Reaction Conditions

Reaction Steps

In a 25 mL round-bottomed flask, 6-vinyl-1H-pyrrolo[2,3-b]pyridine-3-carbonitrile (138 mg, 816 μmol, Eq: 1.00), 6-tert-butyl-8-fluoro-2-(1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-4-yl)phthalazin-1(2H)-one (287 mg, 816 μmol, Eq: 1.00) and copper acetate (200 mg) were combined with 1,2-Dichloroethane (3.58 ml) to give a blue suspension. Pyridine (129 mg, 132 μl, 1.63 mmol, Eq: 2) was added. The reaction mixture was heated to 45° C. and stirred for 2 d. The reaction mixture was poured into 20 mL sat NH4Cl and extracted with sat EtOAc (3×20 mL). The organic layers were dried over MgSO4 and concentrated in vacuo. The crude material was purified by flash chromatography (silica gel, 40 g, 5% to 10% MeOH in DCM), then by HPLC to give 1-(3-(6-tert-butyl-8-fluoro-1-oxophthalazin-2(1H)-yl)-2-(hydroxymethyl)phenyl)-6-vinyl-1H-pyrrolo[2,3-b]pyridine-3-carbonitrile (51 mg, 13%).

Provenance & Evidence