Sodium Iodide → 1-(2,3-Difluoro-4-hydroxyphenyl)-2-(3,5-dimethylisoxazol-4-yl)-1H-indole-3-carbonitrile

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Reaction Conditions

Reaction Steps

To 2-bromo-1-(2,3-difluoro-4-hydroxyphenyl)-1H-indole-3-carbonitrile (Example 103) was added 1.5 eq 3,5-dimethylisooxazole-4-boronic acid, 4 eq potassium carbonate, 2 eq sodium iodide and 10 mol % tetrakis(triphenylphosphine)palladium. DME:H2O (1:1) was added and the vial was flushed with nitrogen, sealed and stirred at 150° C. for 10 min. The reaction mixture was cooled to rt, diluted with H2O and extracted with DCM. The organic phase was evaporated to dryness and purified on silica column using 1:1 n-heptane:EtOAc as mobile phase. ES/MS m/z: 366.20 (M+H), 364.20 (M−H); 1H NMR (CDCl3, 500 MHz): 7.84 (d, 1H), 7.39 (m, 2H), 7.19 (d, 1H), 6.93 (broad m, 2H), 2.42 (s, 1.5H), 2.24 (s, 1.5H), 2.19 (s, 1.5H), 2.01 (s, 1.5H)

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