Tetrahydrofuran → HCID 66834141, compound

HRID 61730Notes

Reaction equation

HRID 61730 reaction equation
[CH2:1]1[CH2:5][O:4][CH2:3][CH2:2]1.[C:6]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(OC(N=NC(OC(C)C)=O)=O)(C)C.[Si](OC1[CH:48]=[CH:49][C:50]2[C:62](=[O:63])[C:61]3[C:60]4[C:55](=[CH:56][C:57]([C:64]#[N:65])=[CH:58][CH:59]=4)[NH:54][C:53]=3[C:52]([CH3:67])([CH3:66])C=2C=1)(C(C)(C)C)(C)C>CO>[CH3:3][O:4][C:5]1[CH:48]=[CH:49][C:50]2[C:62](=[O:63])[C:61]3[C:60]4[C:55](=[CH:56][C:57]([C:64]#[N:65])=[CH:58][CH:59]=4)[N:54]([CH3:6])[C:53]=3[C:52]([CH3:67])([CH3:66])[C:2]=2[CH:1]=1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 66834106HCID 66834106, compound

Product 1

HCID 66834141HCID 66834141, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To the THF solution of triphenylphosphine (260 mg, 3 eq.), azodicarboxylic acid diisopropyl ester (0.195 ml, 3 eq.) was added and the mixture was stirred at room temperature for 1 hr. Thereafter, 8-(tert-butyldimethylsilanyloxy)-6,6-dimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile (Compound A10, 138 mg, 0.331 mmol) and methanol (1 ml) were added and stirred overnight. The reaction solution was purified by HPLC to obtain the target compound (44.8 mg, 41%).

Workup

  1. stirringstirred overnight
  2. customThe reaction solution was purified by HPLC

Sources & evidence

ORD record
ord-27e5562b97ff45808670a582780d0788
Source dataset
uspto-grants-2016_09
Patent number
US09440922B2

Reaction notes

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