Sodium Carbonate → N-(2-chloro-5-(6-phthalazinyl)-3-pyridinyl)-4-fluorobenzenesulfonamide

Beteiligte Stoffe

Reaktionsbedingungen

Reaktionsschritte

A suspension of N-(2-chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-yl)-4-fluorobenzenesulfonamide (102 mg, 247 μmol), 6-bromophthalazine (43 mg, 206 μmol), dichloro[1,1′bis(diphenylphoshino)ferrocene]palladium(II)dichloromethane adduct (11 mg, 15 μmol), and Na2CO3 (65 mg, 617 μmol) in 1,4-dioxane (2 mL) and water (1 mL) was sparged with nitrogen for 5 minutes, then heated to 100° C. for 2 hours. The reaction was then partitioned between 9:1 CHCl3/IPA (30 mL) and 5% NaHCO3 (10 mL). The separated organic was dried over Na2SO4, concentrated onto dry silica, and then purified on silica eluting with 2→5% of MeOH/DCM. Product was isolated as light yellow solid. MS (ESI pos. ion) m/z calc'd for C19H12ClFN4O2S: 414.0; found 415.0. 1H NMR (400 MHz, DMSO-d6) δ 7.44 (t, J=8.8 Hz, 2 H) 7.80-7.87 (m, 2 H) 8.24 (d, J=2.1 Hz, 1 H) 8.32 (d, J=8.4 Hz, 1 H) 8.38 (dd, J=8.7, 2.0 Hz, 1 H) 8.54 (s, 1 H) 8.79 (d, J=2.1 Hz, 1 H) 9.76 (s, 2 H) 10.60 (s, 1 H).

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