Sodium hydride → 2-(6-tert-butyl-8-fluoro-1-oxophthalazin-2(1H)-yl)-4-iodonicotinaldehyde

Beteiligte Stoffe

Reaktionsschritte

In a 1 L round-bottomed flask, 6-tert-butyl-8-fluorophthalazin-1(2H)-one (5.6 g, 25.4 mmol, Eq: 1.00) was combined with THF (300 ml) to give a colorless solution. Sodium hydride (1.12 g, 28.0 mmol, Eq: 1.1) was added. The reaction mixture was stirred at ambient temperature for 10 min. 2-Fluoro-4-iodonicotinaldehyde (7.02 g, 28.0 mmol, Eq: 1.1) was added and the reaction mixture was stirred at ambient temperature for 1 h. The reaction was complete as determined by LCMS analysis. The reaction mixture was quenched with saturated NH4Cl. The reaction mixture was poured into 200 mL H2O and extracted 3× with CH2Cl2. The organic layers were washed with brine, then dried over Na2SO4 and concentrated in vacuo. The resultant bright yellow solid was transferred into a filter funnel and the flask washed twice with a small volume of EtOAc to ensure complete transfer of the solid into the funnel. The liquid was filtered through. The solid was triturated twice with Et2O and dried under vacuum to afford the desired product as a cream-colored solid (8.09 g, 17.9 mmol, 70.5% yield). (M+H)+=452 m/e. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.44 (s, 9 H) 7.49-7.54 (m, 1 H) 7.54 (d, J=1.77 Hz, 1 H) 8.03 (d, J=5.31 Hz, 1 H) 8.30 (d, J=2.53 Hz, 1 H) 8.37 (d, J=5.31 Hz, 1 H) 9.98 (s, 1 H).

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