Diethyl Ether → HCID 68743932, compound

HRID 1946211Notes

Reaction equation

[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([CH:11]=[CH:12][CH:13]=O)=[CH:3]1.[Cl-].[C:16]([C:19]1[CH:20]=[C:21]2[C:25](=[CH:26][CH:27]=1)[NH+:24]=[C:23]([CH3:28])[C:22]2([CH3:30])[CH3:29])([OH:18])=[O:17].CCOCC>CN(C=O)C>[CH3:29][C:22]1([CH3:30])[C:21]2[C:25](=[CH:26][CH:27]=[C:19]([C:16]([O-:18])=[O:17])[CH:20]=2)[N+:24]2[CH:23]=[CH:28][C:11]([C:4]3[C:5]4[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=4)[N:2]([CH3:1])[CH:3]=3)=[CH:12][C:13]1=2

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of 3-(1-methyl-1H-indol-3-yl)prop-2-enal (2.37 g, 12.8 mmol) and 5-carboxy-2,3,3-trimethyl-3H-indolium chloride (3.06 g, 12.8 mmol) in 20 ml of DMF was heated at 120° C. for 17 h. After cooling, ether was added and the solids precipitated. The resulting solids was collected and further purified by silica gel chromatography (eluent: dichloromethane/methanol=10/1 to 2/1) to afford 0.83 g of a yellow powder.

Workup

temperatureAfter cooling
customthe solids precipitated
customThe resulting solids was collected
customfurther purified by silica gel chromatography (eluent: dichloromethane/methanol=10/1 to 2/1)

Sources & evidence

ORD record: ord-3994de2113774c4389d54dced0d3fd41
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08398722B2

Reaction notes

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