Imidazole → HCID 66834106, compound

HRID 61729Notes

Reaction equation

HRID 61729 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][C:5]2[C:17](=[O:18])[C:16]3[C:15]4[C:10](=[CH:11][C:12]([C:19]#[N:20])=[CH:13][CH:14]=4)[NH:9][C:8]=3[C:7]([CH3:22])([CH3:21])[C:6]=2[CH:23]=1.N1C=CN=C1.[C:29]([Si:33](Cl)([CH3:35])[CH3:34])([CH3:32])([CH3:31])[CH3:30].C(=O)([O-])O.[Na+]>CN(C=O)C>[C:29]([Si:33]([CH3:35])([CH3:34])[O:1][C:2]1[CH:3]=[CH:4][C:5]2[C:17](=[O:18])[C:16]3[C:15]4[C:10](=[CH:11][C:12]([C:19]#[N:20])=[CH:13][CH:14]=4)[NH:9][C:8]=3[C:7]([CH3:21])([CH3:22])[C:6]=2[CH:23]=1)([CH3:32])([CH3:31])[CH3:30]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 516892Sodium BicarbonateHCID 668338618-Hydroxy-6,6-dimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile2×

Product 1

HCID 66834106HCID 66834106, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The DMF solution of 8-methoxy-6,6-dimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile (Compound A6, 100 mg, 0.331 mmol), imidazole (67.5 mg, 3 eq.) and tert-butylchlorodimethylsilane (92.4 mg, 1.5 eq.) was stirred overnight at room temperature. To the reaction solution, saturated aqueous solution of sodium hydrogen carbonate was added followed by extraction with tert-butylmethyl ether. The organic layer was washed with brine and dried over sodium sulfate. The drying agent was removed by filtration and the residues obtained after concentration under reduced pressure were purified by silica gel column chromatography (ethyl acetate/hexane) to obtain the target compound (white solid, 170 mg, 100%).

Workup

  1. extractionfollowed by extraction with tert-butylmethyl ether
  2. washThe organic layer was washed with brine
  3. dry with materialdried over sodium sulfate
  4. customThe drying agent was removed by filtration
  5. customthe residues obtained
  6. concentrationafter concentration under reduced pressure
  7. customwere purified by silica gel column chromatography (ethyl acetate/hexane)
  8. customto obtain the target compound (white solid, 170 mg, 100%)

Sources & evidence

ORD record
ord-1aeb59609175470bb44693e08f435bb3
Source dataset
uspto-grants-2016_09
Patent number
US09440922B2

Reaction notes

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