Potassium Iodide → HCID 86680829, compound

HRID 2401684Notes

Reaction equation

[C:1]([C:5]1[CH:6]=[CH:7][C:8]([OH:13])=[C:9]([CH:12]=1)[CH:10]=O)([CH3:4])([CH3:3])[CH3:2].Cl.Cl[CH2:16][C:17]1[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>O.CN(C=O)C>[C:1]([C:5]1[CH:6]=[CH:7][C:8]2[O:13][C:16]([C:17]3[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=3)=[CH:10][C:9]=2[CH:12]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 0.50 g of 5-tert-butyl-2-hydroxybenzaldehyde, 0.48 g of 4-(chloromethyl)pyridine hydrochloride, 0.78 g of potassium carbonate, 0.49 g of potassium iodide and 10 ml of DMF was stirred at 80° C. for 2 hours. Subsequently, 0.78 g of potassium carbonate was added to the reaction mixture, and the mixture was stirred at 150° C. for 8 hours. The reaction mixture was cooled to room temperature. Water was added to the reaction mixture, and the precipitated solid was collected by filtration. This solid was dissolved in ethyl acetate. The organic layer was washed with water and saturated brine and dried over sodium sulfate, then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 0.48 g of 4-(5-tert-butylbenzofuran-2-yl)pyridine (hereinafter, referred to as “Present Active Compound 1”).

Workup

stirringthe mixture was stirred at 150° C. for 8 hours
temperatureThe reaction mixture was cooled to room temperature
filtrationthe precipitated solid was collected by filtration
dissolutionThis solid was dissolved in ethyl acetate
washThe organic layer was washed with water and saturated brine
dry with materialdried over sodium sulfate
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-d9ccbf602cb541c6b18a461d9d461786
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08796306B2

Reaction notes

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