HCID 66793995, compound → HCID 66793950, compound

HRID 1623528Notes

Reaction equation

HRID 1623528 reaction equation
[Cl:1][C:2]1[C:10]([C:11]2[CH:12]=[N:13][CH:14]=[C:15]([CH:17]=[CH2:18])[CH:16]=2)=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][C:5](=[O:20])[N:6]2[CH3:19]>C(O)C.[Pd]>[Cl:1][C:2]1[C:10]([C:11]2[CH:12]=[N:13][CH:14]=[C:15]([CH2:17][CH3:18])[CH:16]=2)=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][C:5](=[O:20])[N:6]2[CH3:19]

Participants

4

Reactant 1

HCID 66793995HCID 66793995, compound

Product 1

HCID 66793950HCID 66793950, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 4-chloro-1-methyl-5-(5-vinyl-pyridin-3-yl)-1,3-dihydro-indol-2-one (70 mg, 0.246 mmol) in ethanol (5 mL) was added 10% palladium on carbon (39 mg, 0.037 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 5%) to afford 4-chloro-5-(5-ethyl-pyridin-3-yl)-1-methyl-1,3-dihydro-indol-2-one. HRMS: (ESI) m/z 287.0946 (M+H)+; 1H NMR (400 MHz, CDCl3) δ ppm 1.33 (t, J=7.6 Hz, 3H), 2.76 (q, J=7.6 Hz, 2H), 3.27 (s 3H), 3.61 (s, 2H), 6.85 (d, J=8.0 Hz, 1H), 7.30 (d, J=8.0 Hz, 1H), 7.68 (s, 1H), 8.45-8.57 (m, 2H).

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 5%)

Sources & evidence

ORD record
ord-1c111fc1fdb34faf949925c49fcde51d
Source dataset
uspto-grants-2014_07
Patent number
US08778972B2

Reaction notes

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