9-(3-Hydroxy-3-methyl-but-1-ynyl)-8-methoxy-6,6-dimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile → 9-(3-Hydroxy-3-methyl-butyl)-8-methoxy-6,6-dimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile

HRID 61790Notes

Reaction equation

HRID 61790 reaction equation
[OH:1][C:2]([CH3:30])([CH3:29])[C:3]#[C:4][C:5]1[C:26]([O:27][CH3:28])=[CH:25][C:8]2[C:9]([CH3:24])([CH3:23])[C:10]3[NH:11][C:12]4[C:17]([C:18]=3[C:19](=[O:20])[C:7]=2[CH:6]=1)=[CH:16][CH:15]=[C:14]([C:21]#[N:22])[CH:13]=4>C(O)C.CN(C)C(=O)C.[Pd]>[OH:1][C:2]([CH3:30])([CH3:29])[CH2:3][CH2:4][C:5]1[C:26]([O:27][CH3:28])=[CH:25][C:8]2[C:9]([CH3:23])([CH3:24])[C:10]3[NH:11][C:12]4[C:17]([C:18]=3[C:19](=[O:20])[C:7]=2[CH:6]=1)=[CH:16][CH:15]=[C:14]([C:21]#[N:22])[CH:13]=4

Participants

5

Reactant 1

HCID 668343479-(3-Hydroxy-3-methyl-but-1-ynyl)-8-methoxy-6,6-dimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile

Product 1

HCID 668341139-(3-Hydroxy-3-methyl-butyl)-8-methoxy-6,6-dimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrileYield 80%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 31374DimethylacetamideSolvent

Procedure

9-(3-Hydroxy-3-methyl-but-1-ynyl)-8-methoxy-6,6-dimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile (Compound E4-2-1, 21.0 mg, 0.0527 mmol) was dissolved in ethanol (15 mL) and N,N-dimethylacetamide (2 mL), added with 10% Pd/C (6.7 mg), and then stirred at room temperature overnight under hydrogen atmosphere. The reaction solution was filtered and concentrated under reduced pressure. The resulting residues were diluted with ethyl acetate, washed with brine, dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The resulting solid was washed with dichloromethane to obtain the title compound (yellow powder, 16.9 mg, 80%).

Workup

  1. filtrationThe reaction solution was filtered
  2. concentrationconcentrated under reduced pressure
  3. additionThe resulting residues were diluted with ethyl acetate
  4. washwashed with brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. washThe resulting solid was washed with dichloromethane

Sources & evidence

ORD record
ord-49f07e661c0346dfa5e4cc57f283a872
Source dataset
uspto-grants-2016_09
Patent number
US09440922B2

Reaction notes

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