Dimethylformamide → HCID 86680834, compound

HRID 2401690Notes

Reaction equation

HRID 2401690 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:7]([C:10]([F:13])([F:12])[F:11])=[CH:6][C:3]=1[CH:4]=O.Cl[CH2:15][C:16]1[CH:21]=[CH:20][N:19]=[CH:18][C:17]=1[F:22].C(=O)([O-])[O-].[K+].[K+].CN(C=O)C>O>[F:22][C:17]1[CH:18]=[N:19][CH:20]=[CH:21][C:16]=1[C:15]1[O:1][C:2]2[CH:9]=[CH:8][C:7]([C:10]([F:13])([F:12])[F:11])=[CH:6][C:3]=2[CH:4]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 155009882-Hydroxy-5-trifluoromethylbenzaldehydeHCID 64950694HCID 64950694, compound

Product 1

HCID 86680834HCID 86680834, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 1.59 g of 2-hydroxy-5-(trifluoromethyl)benzaldehyde, 1.22 g of 4-(chloromethyl)-3-fluoropyridine, 3.48 g of potassium carbonate and 7 ml of DMF was stirred at 80° C. for 1 hour and subsequently 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 1.27 g of 3-fluoro-4-[5-(trifluoromethyl)benzofuran-2-yl]-pyridine (hereinafter, referred to as “Present Active Compound 8”).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionthe mixture was extracted twice with ethyl acetate
  3. washwashed with water and saturated brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f9ef6d8653134c019b7b1e9edbfc02a7
Source dataset
uspto-grants-2014_08
Patent number
US08796306B2

Reaction notes

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