tert-Butyl (triphenylphosphoranylidene) acetate → HCID 67025246, compound

HRID 1512731Notes

Reaction equation

HRID 1512731 reaction equation
C1(P(=[CH:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH:28]([C:30]1[C:38]2[C:33](=[CH:34][C:35]([C:39]#[N:40])=[CH:36][CH:37]=2)[NH:32][CH:31]=1)=O>C(#N)C>[C:39]([C:35]1[CH:34]=[C:33]2[C:38]([C:30](/[CH:28]=[CH:20]/[C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])=[CH:31][NH:32]2)=[CH:37][CH:36]=1)#[N:40]

Participants

4

Reactant 2

HCID 256127tert-Butyl (triphenylphosphoranylidene) acetate5×HCID 107496603-formyl-1H-indole-6-carbonitrile

Product 1

HCID 67025246HCID 67025246, compoundYield 58.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1,1-Dimethylethyl (triphenyl-λ5-phosphanylidene)acetate (1.540 g) was added to a suspension of 3-formyl-1H-indole-6-carbonitrile (D13) (604 mg) in acetonitrile (20 mL) at RT. The reaction mixture was heated to refluxing and stirred for 3.5 hours. Another portion of 1,1-dimethylethyl (triphenyl-λ5-phosphanylidene)acetate (1 g) was added and the resulting suspension was refluxed for 3 more hours. Another portion of 1,1-dimethylethyl (triphenyl-λ5-phosphanylidene)acetate (1 g) was added and the resulting suspension was refluxed for 2.5 more hours. Another portion of 1,1-dimethylethyl (triphenyl-λ5-phosphanylidene)acetate (1 g) was added and the resulting suspension was refluxed for 3 more hours. Another portion of 1,1-dimethylethyl (triphenyl-λ5-phosphanylidene)acetate (1.5 g) was added and the resulting suspension was refluxed for 3.5 more hours. The solvent was evaporated. The residue was purified by Biotage (33% EtOAc in hexane) to afford 1,1-dimethylethyl (2E)-3-(6-cyano-1H-indol-3-yl)-2-propenoate (D14) as a white solid (556 mg). MS (ES): C16H16N2O2 requires 268; found 267.0 (M−H+).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto refluxing
  3. temperaturethe resulting suspension was refluxed for 3 more hours
  4. temperaturethe resulting suspension was refluxed for 2.5 more hours
  5. temperaturethe resulting suspension was refluxed for 3 more hours
  6. temperaturethe resulting suspension was refluxed for 3.5 more hours
  7. customThe solvent was evaporated
  8. customThe residue was purified by Biotage (33% EtOAc in hexane)

Sources & evidence

ORD record
ord-5cc4e1f73ab6449293e8ea161ae49724
Source dataset
uspto-grants-2012_07
Patent number
US08217028B2

Reaction notes

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