Butanal → 1,1-Di-(5-fluoroindol-3-yl)-butane

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[CH:5]2.[CH:11](=O)[CH2:12][CH2:13][CH3:14]>>[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[CH:11]([C:5]1[C:4]2[C:8](=[CH:9][CH:10]=[C:2]([F:1])[CH:3]=2)[NH:7][CH:6]=1)[CH2:12][CH2:13][CH3:14]

Participants

Reactant 2

HCID 261Butanal

HCID 678615-Fluoroindole

Product 1

HCID 220193091,1-Di-(5-fluoroindol-3-yl)-butaneYield 45%

Procedure

This was prepared in the same way as described in example 2/2 starting from 5-fluoroindole and butyraldehyde. The reaction, however, was heated under reflux for 24 hours. The end product was isolated and purified by chromatography on an SiO2 column using a hexane:ethyl ether gradient ranging from 7:3 to 4:6 as the eluent. Yield 45%.

Workup

customThis was prepared in the same way
customThe reaction
temperaturehowever, was heated
temperatureunder reflux for 24 hours
customThe end product was isolated
custompurified by chromatography on an SiO2 column

Sources & evidence

ORD record: ord-40492c21a69f46b88fd0fa2d519864ca
Source dataset: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07084166B2

Reaction notes

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