Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl ester → Ethyl (2E)-3-(7-cyano-6-fluoro-1H-indol-3-yl)-2-propenoate

HRID 1512840Notes

Reaction equation

HRID 1512840 reaction equation
[F:1][C:2]1[C:10]([C:11]#[N:12])=[C:9]2[C:5]([C:6]([CH:13]=O)=[CH:7][NH:8]2)=[CH:4][CH:3]=1.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:10]1[C:2]([F:1])=[CH:3][CH:4]=[C:5]2[C:9]=1[NH:8][CH:7]=[C:6]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 591460486-fluoro-3-formyl-1H-indole-7-carbonitrile

Product 1

HCID 59146028Ethyl (2E)-3-(7-cyano-6-fluoro-1H-indol-3-yl)-2-propenoateYield 58.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a mixture of 6-fluoro-3-formyl-1H-indole-7-carbonitrile (D142) (3 g) in CH3CN (30 mL) was added ethyl (triphenylphosphoranylidene)acetate (11.1 g). The reaction was heated to reflux overnight. After the mixture was filtered, the filtrate was concentrated and purified by column chromatography to afford ethyl (2E)-3-(7-cyano-6-fluoro-1H-indol-3-yl)-2-propenoate (D143) (2.4 g) as a light yellow solid.

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux overnight
  3. filtrationAfter the mixture was filtered
  4. concentrationthe filtrate was concentrated
  5. custompurified by column chromatography

Sources & evidence

ORD record
ord-d2fce5705d54401a834434af9c76a324
Source dataset
uspto-grants-2012_07
Patent number
US08217028B2

Reaction notes

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