Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl ester → Ethyl (2E)-3-(6-cyano-5-fluoro-1H-indol-3-yl)-2-propenoate

HRID 1512849Notes

Reaction equation

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

Participants

Conditions

Temperature: 90 °C

Procedure

To a solution of 5-fluoro-3-formyl-1H-indole-6-carbonitrile (D152) (250 mg) in acetonitrile (30 mL) was added ethyl (triphenylphosphoranylidene)acetate (926 mg). The reaction mixture was refluxed at 90° C. for 24 hours. The solvent was then evaporated and the residue was chromatographed on silica gel eluting with EA and PA (3:7-7:3) to generate ethyl (2E)-3-(6-cyano-5-fluoro-1H-indol-3-yl)-2-propenoate (D153) (275 mg). MS (ES): C14H11FN2O2 requires 258.1; found 259.1 (M+H+).

Workup

customThe solvent was then evaporated
customthe residue was chromatographed on silica gel eluting with EA and PA (3:7-7:3)

Sources & evidence

ORD record: ord-97a28c2498de4a69a8809d630c3998ba
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08217028B2

Reaction notes

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