Acetyl chloride → 1-(2-phenyl-1H-indol-3-yl)ethanone

HRID 966061Notes

Reaction equation

HRID 966061 reaction equation
[C:1]1([C:7]2[NH:8][C:9]3[C:14]([CH:15]=2)=[CH:13][CH:12]=[CH:11][CH:10]=3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:16](Cl)(=[O:18])[CH3:17].[Sn](Cl)(Cl)(Cl)Cl>C(Cl)Cl>[C:16]([C:15]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[NH:8][C:7]=1[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)(=[O:18])[CH3:17]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 136982-PhenylindoleHCID 24287Tin tetrachloride

Product 1

HCID 6133641-(2-phenyl-1H-indol-3-yl)ethanone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 2-phenylindole (193.3 mg, 1.0 mmol) and acetyl chloride (92 μL, 1.3 mmol) in CH2Cl2 is treated with tin tetrachloride (97.4 μL, 1.9 mmol) at room temperature, shaken for 6 h, quenched with saturated NaHCO3 and extracted with ethyl acetate. The extracts are combined and concentrated in vacuo to afford the 3-acetyl-2-phenylindole intermediate. A suspension of the thus-obtained 3-acetyl-2-phenylindole (47 mg, 0.2 mmol) in isopropanol and concentrated HCl (5 μL) is treated with aminoguanidine bicarbonate, heated at 80° C. for 2 h, cooled to room temperature and concentrated in vacuo. The resultant residue is purified by HPLC to afford the title product, 21.0 mg (36% yield), identified by HPLC1 and mass spectral analyses, (M+H) 292, retention time 3.9 min.

Workup

  1. customquenched with saturated NaHCO3
  2. extractionextracted with ethyl acetate
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9ffef4f885c34428b5e1c7fc2245c86a
Source dataset
uspto-grants-2005_10
Patent number
US06951881B2

Reaction notes

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