tert-Butyl (triphenylphosphoranylidene) acetate → HCID 59146100, compound

HRID 1512725Notes

Reaction equation

HRID 1512725 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](=[C:34]([C:39]#[N:40])[CH:35]=[CH:36][CH:37]=2)[NH:32][CH:31]=1)=O>C(#N)C>[C:39]([C:34]1[CH:35]=[CH:36][CH:37]=[C:38]2[C:33]=1[NH:32][CH:31]=[C:30]2/[CH:28]=[CH:20]/[C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])#[N:40]

Participants

4

Reactant 2

HCID 256127tert-Butyl (triphenylphosphoranylidene) acetate2×HCID 210715333-Formyl-1H-indole-7-carbonitrile

Product 1

HCID 59146100HCID 59146100, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1,1-Dimethylethyl (triphenyl-λ5-phosphanylidene)acetate (1.858 g) was added to a suspension of 3-formyl-1H-indole-7-carbonitrile (D3) (0.7 g) in acetonitrile (70 mL). The reaction mixture was heated to reflux and stirred for 2.5 hours. Another portion of 1,1-dimethylethyl (triphenyl-λ5-phosphanylidene)acetate (0.3 g) was added and the resulting suspension was refluxed for 2 more hours. The solvent was evaporated. The residue was purified by Biotage (25% EtOAc in hexane) to afford 1,1-dimethylethyl (2E)-3-(7-cyano-1H-indol-3-yl)-2-propenoate (D4) as a white solid (850 mg). δH (DMSO-d6, 400 MHz): 1.49 (9H, s), 6.40 (1H, d), 7.30 (1H, t), 7.71 (1H, dd), 7.79 (1H, d), 8.11 (1H, s), 8.25 (1H, dd), 12.59 (1H, br s). MS (ES): C16H16N2O2 requires 268; found 267.1 (M−H+).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux
  3. temperaturethe resulting suspension was refluxed for 2 more hours
  4. customThe solvent was evaporated
  5. customThe residue was purified by Biotage (25% EtOAc in hexane)

Sources & evidence

ORD record
ord-0770faf9aa9247b8aced21cb1bbaa765
Source dataset
uspto-grants-2012_07
Patent number
US08217028B2

Reaction notes

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