Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl ester → ethyl (2E)-3-(7-cyano-4-fluoro-1H-indol-3-yl)-2-propenoate

HRID 1512756Notes

Reaction equation

HRID 1512756 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:8]([C:11]#[N:12])=[C:7]2[C:3]=1[C:4]([CH:13]=O)=[CH:5][NH:6]2.C1(P(=[CH:34][C:35]([O:37][CH2:38][CH3:39])=[O:36])(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>CC#N>[C:11]([C:8]1[CH:9]=[CH:10][C:2]([F:1])=[C:3]2[C:7]=1[NH:6][CH:5]=[C:4]2/[CH:13]=[CH:34]/[C:35]([O:37][CH2:38][CH3:39])=[O:36])#[N:12]

Participants

4

Reactant 2

HCID 70670Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl esterHCID 591461794-fluoro-3-formyl-1H-indole-7-carbonitrile

Product 1

HCID 59146086ethyl (2E)-3-(7-cyano-4-fluoro-1H-indol-3-yl)-2-propenoateYield 74.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a mixture of 4-fluoro-3-formyl-1H-indole-7-carbonitrile (D42) (9.0 g) in CH3CN (120 mL) was added ethyl (triphenylphosphoranyliden)acetate (25.0 g). The reaction was heated at reflux overnight. After the mixture was filtered, the filtrate was concentrated and purified by preparative TLC to afford ethyl (2E)-3-(7-cyano-4-fluoro-1H-indol-3-yl)-2-propenoate (D43) (9.2 g) as a yellow solid.

Workup

  1. temperatureThe reaction was heated
  2. temperatureat reflux overnight
  3. filtrationAfter the mixture was filtered
  4. concentrationthe filtrate was concentrated
  5. custompurified by preparative TLC

Sources & evidence

ORD record
ord-392de1bb2bc941bc9b766812e9454981
Source dataset
uspto-grants-2012_07
Patent number
US08217028B2

Reaction notes

Loading…