Acetanilide → HCID 15151164, compound

HRID 1366814Notes

Reaction equation

HRID 1366814 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-61208771a965425f8e9bbc798efe115f
Source dataset
uspto-grants-2011_02
Patent number
US07893084B2

Reaction notes

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