Triphenylphosphine → 7-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl methoxy)-6,6-dimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile

HRID 61860

Reaction equation

HRID 61860 reaction equation
[CH3:1][O:2][C:3]1[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]=[CH:5][CH:4]=1)=[CH:16][CH:15]=[C:14]([C:21]#[N:22])[CH:13]=4.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH3:44][C:45]1([CH3:52])[O:49][C@H:48](CO)[CH2:47][O:46]1.N(C(OCC)=O)=NC(OCC)=O>C(OCC)(=O)C.C1(C)C=CC=CC=1.C1COCC1>[CH3:44][C:45]1([CH3:52])[O:49][C@H:48]([CH2:1][O:2][C:3]2[C:8]3[C:9]([CH3:24])([CH3:23])[C:10]4[NH:11][C:12]5[C:17]([C:18]=4[C:19](=[O:20])[C:7]=3[CH:6]=[CH:5][CH:4]=2)=[CH:16][CH:15]=[C:14]([C:21]#[N:22])[CH:13]=5)[CH2:47][O:46]1

Participants

8

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 736056(R)-SolketalHCID 668352707-methoxy-6,6-dimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile

Product 1

HCID 668345317-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl methoxy)-6,6-dimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile

Reagents, catalysts & solvents 3

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

Under nitrogen atmosphere, 7-methoxy-6,6-dimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile (Compound W3, 15 mg, 0.05 mmol) and triphenylphosphine (40 mg, 3 eq.) were added with THF (1 ml), further added dropwise with ((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-methanol (20 mg, 3 eq.) and 2.19 N toluene solution of diethyl azodicarboxylate (68 μL, 3 eq.), and the mixture was stirred at 50° C. for 2 hr. After cooling, the reaction solution was added with ethyl acetate, washed with brine, dried over sodium sulfate, and filtered. The residues obtained after concentration under reduced pressure were purified by preparative TLC (ethyl acetate/dichloromethane), and the resulting solid was washed with dichloromethane to obtain the target compound (brown powder, 5 mg).

Workup

  1. temperatureAfter cooling
  2. washwashed with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. customThe residues obtained
  6. concentrationafter concentration under reduced pressure
  7. customwere purified by preparative TLC (ethyl acetate/dichloromethane)
  8. washthe resulting solid was washed with dichloromethane
  9. customto obtain the target compound (brown powder, 5 mg)

Sources & evidence

ORD record
ord-4b8e140ba2db4cb3834f3c390b3c7ae3
Source dataset
uspto-grants-2016_09
Patent number
US09440922B2

Linked notes

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