3-Fluoroaniline → N-(tert-butyl)-5-(4-((3-fluorophenyl)amino)-5-phenylphthalazin-1-yl)pyridine-3-sulfonamide

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Reaction Steps

N-(tert-Butyl)-5-(4-chloro-5-phenylphthalazin-1-yl)pyridine-3-sulfonamide (1.00 g, 2.21 mmol) in 3-fluoroaniline (2.94 g, 26.5 mmol) was heated in a sealed tube at 100° C. for 12 h. On cooling, the volatile components were removed under reduced pressure and the resulting residue was purified by combiflash (REDISEP®, silica gel, 24 g, 60% EtOAc/hexanes) to obtain N-(tert-butyl)-5-(4-((3-fluorophenyl)amino)-5-phenylphthalazin-1-yl)pyridine-3-sulfonamide (0.70 g, 60%) as a brown solid. LCMS (Condition 11): retention time 1.20 min, [M+1]=528.4. 1H NMR (400 MHz, DMSO-d6) δ 1.94 (s, 9 H), 6.50 (dd, J=1.2 Hz, J=8.4 Hz, 1 H), 6.76 (td, J=2.5 Hz, J=8.4 Hz, 1 H), 7.19-7.25 (m, 2 H), 7.53-7.66 (m, 6 H), 7.88-7.93 (m, 3 H), 8.05 (dd, J=6.8 Hz, J=8.4 Hz, 1 H), 8.54 (t, J=2.0 Hz, 1 H), 9.15 (d, J=2.0 Hz, 1 H), 9.16 (d, J=2.0 Hz, 1 H).

Provenance & Evidence