1-Methyl-5-(4-vinyl-pyridin-3-yl)-1,3-dihydro-indol-2-one → HCID 66788362, compound
Reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][C:7]([C:11]3[CH:12]=[N:13][CH:14]=[CH:15][C:16]=3[CH:17]=[CH2:18])=[CH:8][CH:9]=2)[CH2:4][C:3]1=[O:19]>C(O)C.[Pd]>[CH2:17]([C:16]1[CH:15]=[CH:14][N:13]=[CH:12][C:11]=1[C:7]1[CH:6]=[C:5]2[C:10](=[CH:9][CH:8]=1)[N:2]([CH3:1])[C:3](=[O:19])[CH2:4]2)[CH3:18]Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
To a solution of 1-methyl-5-(4-vinyl-pyridin-3-yl)-1,3-dihydro-indol-2-one (30 mg, 0.12 mmol) in ethanol (1 mL) was added 10% palladium on carbon (18 mg, 0.02 mmol). The atmosphere over the reaction mixture was evacuated and the reaction was placed under an atmosphere of hydrogen gas via a balloon. The reaction was stirred for 25 minutes. The reaction mixture was then filtered through a plug of Celite® and the filtrate was then concentrated to dryness. The resulting residue was purified by silica gel flash chromatography (ethanol-dichloromethane, 0 to 6%) to afford 5-(4-ethyl-pyridin-3-yl)-1-methyl-1,3-dihydro-indol-2-one. The HCl salt of the title compound was prepared by dissolution in diethyl ether followed by treatment with an excess of 1N HCl in diethyl ether. The resulting heterogeneous solution was concentrated to furnish the HCl salt of 5-(4-ethyl-pyridin-3-yl)-1-methyl-1,3-dihydro-indol-2-one. HRMS: (ESI) m/z 253.1335 (M+H)+; 1H NMR (400 MHz, CD3OD) δ ppm 1.23 (t, J=7.6 Hz, 3H), 2.93 (q, J=7.6 Hz, 2H), 3.28 (s, 3H), 3.66 (s, 2H), 7.16 (d, J=8.6 Hz, 1H), 7.33-7.43 (m, 2H), 8.05 (d, J=6.3 Hz, 1H), 8.65 (s, 1H), 8.71 (d, J=6.1 Hz, 1H).