Potassium Phosphate, Tribasic → 4-(1H-indol-4-ylamino)-5-[4-methoxy-3-(2-methoxyethoxy)phenyl]nicotinonitrile

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Reaction Conditions

Reaction Steps

To a stirred solution of 4-chloro-5-[4-methoxy-3-(2-methoxyethoxy)phenyl]-nicotinonitrile (100 mg, 0.313 mmol), 4-aminoindole (62 mg, 0.47 mmol), DavePhos (37 mg, 0.094 mmol), and K3PO4 (99.8 mg, 0.47 mmol) in 4 mL of anhydrous ethylene glycol dimethyl ether was added Pd2(dba)3 (28.7 mg, 0.031 mmol). The mixture was heated to 90° C. for 2 h, then cooled, filtered through celite, concentrated in vacuo, and crystallized by tritration with ether/hexane to yield 42.5 mg (33% yield) of the title compound 153 as a tan solid. MS: 415.1 (M+H), HPLC retention time: 7.70 min(b).

Provenance & Evidence