Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl ester → Ethyl (2E)-3-(5-cyano-1H-indol-2-yl)-2-propenoate

HRID 1512743Notes

Reaction equation

[CH:1]([C:3]1[NH:4][C:5]2[C:10]([CH:11]=1)=[CH:9][C:8]([C:12]#[N:13])=[CH:7][CH:6]=2)=O.C1(P(=[CH:33][C:34]([O:36][CH2:37][CH3:38])=[O:35])(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(#N)C>[C:12]([C:8]1[CH:9]=[C:10]2[C:5](=[CH:6][CH:7]=1)[NH:4][C:3](/[CH:1]=[CH:33]/[C:34]([O:36][CH2:37][CH3:38])=[O:35])=[CH:11]2)#[N:13]

Participants

Conditions

Temperature: 60 °C

Procedure

2-Formyl-1H-indole-5-carbonitrile (D28) (230 mg) was dissolved in acetonitrile (50 mL). Ethyl (triphenyl-λ5-phosphanylidene)acetate (522 mg) was added to the solution. The reaction was heated to 60° C. and was stirred at 60° C. for 1 hour. The reaction mixture was concentrated. The residue was purified by Biotage (25%→33% EtOAc in hexane) to afford ethyl (2E)-3-(5-cyano-1H-indol-2-yl)-2-propenoate (D29) (230 mg) as a white solid. MS (ES): C14H12N2O2 requires 240; found 239.1 (M−H+).

Workup

concentrationThe reaction mixture was concentrated
customThe residue was purified by Biotage (25%→33% EtOAc in hexane)

Sources & evidence

ORD record: ord-0fed45fffa114d73aad457312be209c9
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08217028B2

Reaction notes

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