Dimethylformamide → HCID 86680836, compound

HRID 2401692Notes

Reaction equation

HRID 2401692 reaction equation
[F:1][CH:2]([F:5])[CH2:3][OH:4].CN(C=O)C.[H-].[Na+].F[C:14]1[CH:15]=[N:16][CH:17]=[CH:18][C:19]=1[C:20]1[O:21][C:22]2[CH:28]=[CH:27][C:26]([C:29]([F:32])([F:31])[F:30])=[CH:25][C:23]=2[CH:24]=1>O>[F:1][CH:2]([F:5])[CH2:3][O:4][C:14]1[CH:15]=[N:16][CH:17]=[CH:18][C:19]=1[C:20]1[O:21][C:22]2[CH:28]=[CH:27][C:26]([C:29]([F:31])([F:32])[F:30])=[CH:25][C:23]=2[CH:24]=1

Participants

6

Reactant 4

HCID 6228Dimethylformamide3×HCID 24758Sodium hydride2×HCID 1361872,2-Difluoroethan-1-ol2×HCID 86680834HCID 86680834, compound

Product 1

HCID 86680836HCID 86680836, compoundYield 81.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 75 mg of 2,2-difluoroethanol and 0.5 ml of DMF was added to a mixture of 36 mg of sodium hydride (60%, oil-based) and 3 ml of DMF under ice-cooling. This mixture was stirred at room temperature for 15 minutes, and then ice-cooled. Subsequently, 0.20 g of 3-fluoro-4-[5-(trifluoromethyl)benzofuran-2-yl]pyridine was added thereto, and the mixture was stirred at room temperature for 3.5 hours. Thereto was added a mixture of 29 mg of 2,2-difluoroethanol, 0.5 ml of DMF and 14 mg of sodium hydride (60%, oil-based), and the mixture was stirred at room temperature for 1.5 hours. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was 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 3-(2,2-difluoroethoxy)-4-[5-(trifluoromethyl)benzofuran-2-yl]pyridine (hereinafter, referred to as “Present Active Compound 10”).

Workup

  1. temperaturecooling
  2. temperatureice-cooled
  3. stirringthe mixture was stirred at room temperature for 3.5 hours
  4. additionThereto was added
  5. stirringthe mixture was stirred at room temperature for 1.5 hours
  6. extractionthe mixture was extracted with ethyl acetate
  7. washThe organic layer was washed with water and saturated brine
  8. dry with materialdried over magnesium sulfate
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b773fc981b8f48f3bd96496384734ec4
Source dataset
uspto-grants-2014_08
Patent number
US08796306B2

Reaction notes

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