Potassium Iodide → HCID 86680830, compound
Reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:7]([C:10]([F:16])([F:15])[C:11]([F:14])([F:13])[F:12])=[CH:6][C:3]=1[CH:4]=O.Cl.Cl[CH2:19][C:20]1[CH:25]=[CH:24][N:23]=[CH:22][CH:21]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>O.CN(C=O)C>[F:15][C:10]([F:16])([C:7]1[CH:8]=[CH:9][C:2]2[O:1][C:19]([C:20]3[CH:25]=[CH:24][N:23]=[CH:22][CH:21]=3)=[CH:4][C:3]=2[CH:6]=1)[C:11]([F:14])([F:13])[F:12]Participants
Conditions
- Temperature
- 150 °C
Procedure
A mixture of 0.60 g of 2-hydroxy-5-(pentafluoroethyl)benzaldehyde, 0.41 g of 4-(chloromethyl)pyridine hydrochloride, 1.21 g of potassium carbonate, 0.41 g of potassium iodide and 10 ml of DMF was stirred at 80° C. for 2 hours and subsequently at 150° C. for 3 hours. Thereto was added 0.8 g of potassium carbonate, and the mixture was stirred at 150° C. for 2 hours. The reaction mixture was cooled to room temperature. Water was added to the reaction mixture, and the mixture was extracted twice with ethyl acetate. The organic layers were combined and washed with water and saturated brine and dried over magnesium sulfate, then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 0.20 g of 4-[5-(pentafluoroethyl)benzofuran-2-yl]pyridine (hereinafter, referred to as “Present Active Compound 5”).
Workup
- stirringthe mixture was stirred at 150° C. for 2 hours
- temperatureThe reaction mixture was cooled to room temperature
- extractionthe mixture was extracted twice with ethyl acetate
- washwashed with water and saturated brine
- dry with materialdried over magnesium sulfate
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-350513ae3448427c86a19c0fa6e270ed
- Source dataset
- uspto-grants-2014_08
- Patent number
- US08796306B2
Reaction notes
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