HCID 67377908, compound → HCID 67378046, compound

HRID 877517Notes

Reaction equation

HRID 877517 reaction equation
[CH:1](=[C:8]1[CH2:20][CH2:19][C:18]2[C:17]3[C:12](=[CH:13][CH:14]=[C:15]([Cl:22])[C:16]=3[Cl:21])[NH:11][C:10]=2[C:9]1=[O:23])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>CCOC(C)=O.[Pd]>[CH2:1]([CH:8]1[CH2:20][CH2:19][C:18]2[C:17]3[C:12](=[CH:13][CH:14]=[C:15]([Cl:22])[C:16]=3[Cl:21])[NH:11][C:10]=2[C:9]1=[O:23])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 67377908HCID 67377908, compound

Product 1

HCID 67378046HCID 67378046, compoundYield 61%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

2-Benzylidene-5,6-dichloro-2,3,4,9-tetrahydro-1H-carbazol-1-one (0.7 g, 2.05 mmol) was dissolved in EtOAc (150 mL) and 10% Pd/C (0.070 g) was added under N2 atmosphere. The reaction mixture was stirred under H2 atmosphere at room temperature for 12 h then filtered through a Celite® pad. The Celite® pad was washed with EtOAc (2×20 mL) and the filtrate was concentrated in vacuo to provide the crude material which was purified by silica gel chromatography [EtOAc-hexane (1:9) as eluant] to obtain the title compound as a light green solid (0.43 g, 61%). 1H NMR (500 MHz, CDCl3, δ in ppm) 9.03 (bs, 1H), 7.37 (d, J=9.0 Hz, 1H), 7.34-7.30 (m, 3H), 7.25-7.22 (m, 3H), 3.50-3.42 (m, 2H), 3.17-3.10 (m, 1H), 2.87-2.82 (m, 1H), 2.72-2.67 (m, 1H), 2.25-2.21 (m, 1H), 1.97-1.90 (m, 1H).

Workup

  1. filtrationthen filtered through a Celite® pad
  2. washThe Celite® pad was washed with EtOAc (2×20 mL)
  3. concentrationthe filtrate was concentrated in vacuo
  4. customto provide the crude material which
  5. customwas purified by silica gel chromatography [EtOAc-hexane (1:9) as eluant]

Sources & evidence

ORD record
ord-6907aeeff721474b990ad87e1f6a072e
Source dataset
uspto-grants-2015_03
Patent number
US08987319B2

Reaction notes

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