2H-Indol-2-one, 5-(4-ethenyl-3-pyridinyl)-1,3-dihydro-1-methyl- → HCID 66788362, compound

HRID 1623502Notes

Reaction equation

HRID 1623502 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

HCID 667939262H-Indol-2-one, 5-(4-ethenyl-3-pyridinyl)-1,3-dihydro-1-methyl-

Product 1

HCID 66788362HCID 66788362, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

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).

Workup

  1. customThe atmosphere over the reaction mixture was evacuated
  2. filtrationThe reaction mixture was then filtered through a plug of Celite®
  3. concentrationthe filtrate was then concentrated to dryness
  4. customThe resulting residue was purified by silica gel flash chromatography (ethanol-dichloromethane, 0 to 6%)

Sources & evidence

ORD record
ord-7a3187a14b3d417991560d58243aad2b
Source dataset
uspto-grants-2014_07
Patent number
US08778972B2

Reaction notes

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