8-Methoxy-6,6-dimethyl-11-oxo-9-vinyl-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile → 9-Ethyl-8-methoxy-6,6-dimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile

HRID 61788Notes

Reaction equation

HRID 61788 reaction equation
[CH3:1][O:2][C:3]1[C:4]([CH:25]=[CH2:26])=[CH:5][C:6]2[C:18](=[O:19])[C:17]3[C:16]4[C:11](=[CH:12][C:13]([C:20]#[N:21])=[CH:14][CH:15]=4)[NH:10][C:9]=3[C:8]([CH3:23])([CH3:22])[C:7]=2[CH:24]=1>[C].[Pd].C(OCC)(=O)C>[CH2:25]([C:4]1[C:3]([O:2][CH3:1])=[CH:24][C:7]2[C:8]([CH3:23])([CH3:22])[C:9]3[NH:10][C:11]4[C:16]([C:17]=3[C:18](=[O:19])[C:6]=2[CH:5]=1)=[CH:15][CH:14]=[C:13]([C:20]#[N:21])[CH:12]=4)[CH3:26]

Participants

4

Reactant 1

HCID 668341898-Methoxy-6,6-dimethyl-11-oxo-9-vinyl-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile

Product 1

HCID 668342939-Ethyl-8-methoxy-6,6-dimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrileYield 13.3%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8857Ethyl AcetateSolvent

Procedure

The ethyl acetate suspension of 8-methoxy-6,6-dimethyl-11-oxo-9-vinyl-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile (Compound E4-3, 25 mg, 0.07 mmol) and palladium carbon (25 mg) were stirred at room temperature for 1 hr under hydrogen atmosphere. The reaction solution was filtered through Celite. The filtrate was concentrated under reduced pressure and the resulting residues were purified by high performance liquid chromatography to obtain the title compound (white solid, 3.2 mg, 13%).

Workup

  1. filtrationThe reaction solution was filtered through Celite
  2. concentrationThe filtrate was concentrated under reduced pressure
  3. customthe resulting residues were purified by high performance liquid chromatography

Sources & evidence

ORD record
ord-64a8cd4b24794874876debb40143df0b
Source dataset
uspto-grants-2016_09
Patent number
US09440922B2

Reaction notes

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