2-Phenyl-1H-indole-3-carbaldehyde → HCID 178513138, compound

HRID 966060Notes

Reaction equation

[C:1]1([C:7]2[NH:8][C:9]3[C:14]([C:15]=2[CH:16]=O)=[CH:13][CH:12]=[CH:11][CH:10]=3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(=O)(O)O.[NH2:22][NH:23][C:24]([NH2:26])=[NH:25]>C(O)(C)C.Cl>[C:1]1([C:7]2[NH:8][C:9]3[C:14]([C:15]=2[CH:16]=[N:22][NH:23][C:24](=[NH:25])[NH2:26])=[CH:13][CH:12]=[CH:11][CH:10]=3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of DMF (11.0 mL, 142 mmol) and phosphorous oxychloride (3.63 mL, 39 mmol) is stirred at 0° C. for 1 h, a 0.2 mL portion is pipetted into a solution of 2-phenylindole (96 mg, 0.5 mmol) in DMF at 5° C. This reaction mixture is stirred at 5°-10° C. for 1 h, quenched with water, stored at −200 for 16 h and filtered. The filtercake is washed with water and dried in vacuo to afford the 2-phenylindole-3-carboxaldehyde intermediate. A suspension of the thus-obtained 2-phenylindole-3-carboxaldehyde (44.2 mg, 0.2 mmol) in isopropanol and concentrated HCl (50 μL) is treated with aminoguanidine bicarbonate (27 mg, 0.2 mmol), 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, 28 mg (20% yield), identified by mass spectral and HPLC analyses (M+H) 277; retention time 3.76 min.

Workup

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

Sources & evidence

ORD record: ord-6ee6f18e123f46bfad902d60cc62044f
Source dataset: uspto-grants-2005_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06951881B2

Reaction notes

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