Pyridine → (E)-1-methyl-2-oxo-1'-(3-(2-(trifluoromethyl) phenyl)acryloyl)spiro[indoline-3,4'-piperidine]-5-carbonitrile

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Reaction Steps

A solution of trifluoroacetic anhydride (34 mg, 0.157 mmol) in dioxane (4 mL) was added dropwise to a stirred, ice-cooled solution of (E)-1-methyl-2-oxo-1′-(3-(2-(trifluoromethyl)phenyl)acryloyl)spiro[indoline-3,4′-piperidine]-5-carboxamide (60 mg, 0.131 mmol) and pyridine (60 mg, 0.262 mmol). The reaction mixture was stirred at rt overnight. The mixture was diluted with water and extracted with EtOAc. The organic layer was dried over Na2SO4 and concentrated to afford the crude product. After purification by preparative HPLC, (E)-1-methyl-2-oxo-1′-(3-(2-(trifluoromethyl) phenyl)acryloyl)spiro[indoline-3,4′-piperidine]-5-carbonitrile was obtained (2.04 mg, 4%). 1H NMR: (400 MHz, CDCl3): δ=1.85 (m, 4H), 3.20 (m, 3H), 3.80-3.90 (m, 2H), 4.10 (m, 1H), 4.35 (m, 1H), 6.75 (m, 1H), 6.85 (m, 1H), 7.40 (m, 2H), 7.50 (m, 1H), 7.55 (m, 1H) 7.65 (m, 2H), 7.90 (m, 1H).

Provenance & Evidence