Dimethylacetamide → 9-((R)-2,3-Dihydroxy-propoxy)-6,6-dimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile

HRID 61810Notes

Reaction equation

HRID 61810 reaction equation
Br[C:2]1[CH:14]=[C:13]2[C:5]([C:6]3[C:7](=[O:30])[C:8]4[CH:20]=[C:19]([O:21][CH2:22][C@H:23]5[CH2:27][O:26]C(C)(C)[O:24]5)[CH:18]=[CH:17][C:9]=4[C:10]([CH3:16])([CH3:15])[C:11]=3[NH:12]2)=[CH:4][CH:3]=1.[Cu](C#N)[C:32]#[N:33].CC(N(C)C)=O>O>[OH:24][C@H:23]([CH2:27][OH:26])[CH2:22][O:21][C:19]1[CH:18]=[CH:17][C:9]2[C:10]([CH3:15])([CH3:16])[C:11]3[NH:12][C:13]4[C:5]([C:6]=3[C:7](=[O:30])[C:8]=2[CH:20]=1)=[CH:4][CH:3]=[C:2]([C:32]#[N:33])[CH:14]=4

Participants

5

Reactant 3

HCID 31374DimethylacetamideHCID 668343293-Bromo-9-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl methoxy)-6,6-dimethyl-5,6-dihydro-benzo[b]carbazol-11-oneHCID 178418260HCID 178418260, compound

Product 1

HCID 668350169-((R)-2,3-Dihydroxy-propoxy)-6,6-dimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrileYield 22%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

3-Bromo-9-((S)-2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy)-6,6-dimethyl-5,6-dihydro-benzo[b]carbazol-11-one (Compound JJ3-1, 49.5 mg, 0.105 mmol) and copper cyanide (90%, 35.3 mg, 3.4 eq.) were added with DMA (0.5 mL), and the mixture was irradiated with microwave at 200° C. for 1 hr under nitrogen atmosphere. After cooling, the reaction solution was added with water and extracted with ethyl acetate. The insoluble matters were separated off by filtration, and the organic layer was washed with brine and dried over magnesium sulfate. After filtration and the concentration under reduced pressure, the resulting residues were purified by preparative TLC (methanol/dichloromethane) to obtain the title compound (white solid, 8.5 mg, 22%).

Workup

  1. customthe mixture was irradiated with microwave at 200° C. for 1 hr under nitrogen atmosphere
  2. temperatureAfter cooling
  3. extractionextracted with ethyl acetate
  4. customThe insoluble matters were separated off by filtration
  5. washthe organic layer was washed with brine
  6. dry with materialdried over magnesium sulfate
  7. filtrationAfter filtration
  8. concentrationthe concentration under reduced pressure
  9. customthe resulting residues were purified by preparative TLC (methanol/dichloromethane)

Sources & evidence

ORD record
ord-cc536b7883b84f6681d85db2b8d9e7b5
Source dataset
uspto-grants-2016_09
Patent number
US09440922B2

Reaction notes

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