1-(2-phenyl-1H-indol-3-yl)ethanone → HCID 178465621, compound

HRID 966062Notes

Reaction equation

[C:1]([C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][C:5]=1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)(=O)[CH3:2].C(=O)(O)O.[NH2:23][NH:24][C:25]([NH2:27])=[NH:26]>C(O)(C)C.Cl>[C:13]1([C:5]2[NH:6][C:7]3[C:12]([C:4]=2[C:1](=[N:23][NH:24][C:25](=[NH:26])[NH2:27])[CH3:2])=[CH:11][CH:10]=[CH:9][CH:8]=3)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

Conditions

Temperature: 80 °C

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

temperaturecooled to room temperature
concentrationconcentrated in vacuo
customThe resultant residue is purified by HPLC

Sources & evidence

ORD record: ord-6a2baf97cd164376baf17c7dba1b0de9
Source dataset: uspto-grants-2005_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06951881B2

Reaction notes

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