Acetanilide → HCID 15151164, compound

HRID 723632Notes

Reaction equation

HRID 723632 reaction equation
C([NH:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)(=O)C.[C:11]1([C:17]#[CH:18])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[CH3:19][CH2:20][O:21][C:22](C)=[O:23]>O1CCOCC1.CN(C)C(=N)N(C)C.CCCCCC.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]I>[C:11]1([C:17]2[NH:4][C:5]3[C:6]([CH:18]=2)=[CH:7][C:8]([C:22]([O:21][CH2:20][CH3:19])=[O:23])=[CH:9][CH:10]=3)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

9

Reactant 3

HCID 904AcetanilideHCID 8857Ethyl AcetateHCID 10821Phenylacetylene

Product 1

HCID 15151164HCID 15151164, compoundYield 82%

Reagents, catalysts & solvents 5

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 8058HexaneSolventHCID 312751,4-DioxaneSolventHCID 664601,1,3,3-TetramethylguanidineSolvent

Procedure

Following the procedure of A. Bedeschi et al. (Tet. Lett. 1997, 38, 2307), the acetanilide derivative from above (0.900 g, 2.7 mmol) was reacted with phenylacetylene (0.385 mL, 3.5 mmol, 1.3 equivalent) in the presence of PdCl2(PPh3)2 (10 mole %) and CuI (10 mole %) in a mixture of dioxane (5 mL) and tetramethylguanidine (5 mL). The desired 2-phenylindole (0.589 g, 82% yield) was isolated as a yellow solid after flash chromatography with 15% EtOAc in hexane.

Sources & evidence

ORD record
ord-0bb3e91adf5549b98cb0942706b61ce5
Source dataset
uspto-grants-2006_11
Patent number
US07141574B2

Reaction notes

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