Water → HCID 71238257, compound

HRID 340091Notes

Reaction equation

HRID 340091 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[OH:8].[H-].[Na+].[CH3:11][O:12][C:13]([C:15]1[CH:20]=[N:19][C:18](Cl)=[CH:17][N:16]=1)=[O:14].O>CN(C=O)C>[CH3:11][O:12][C:13]([C:15]1[CH:20]=[N:19][C:18]([O:8][C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[F:1])=[CH:17][N:16]=1)=[O:14]

Participants

6

Reactant 4

HCID 962WaterHCID 97072-FluorophenolHCID 24758Sodium hydride2×HCID 406081Methyl 5-chloropyrazine-2-carboxylate

Product 1

HCID 71238257HCID 71238257, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

2-Fluorophenol (21.6 g, 233 mmol) was dissolved in DMF (250 mL) under a calcium chloride drying tube. The solution was cooled to 0° C., and then 60% NaH in paraffin oil (9.3 g, 233 mmol) was added in small portions. After the main portion of NaH had dissolved, 5-chloro-pyrazine-2-carboxylic acid methyl ester (Preparation 41, 40.2 g, 233 mmol) was added. The mixture was refluxed for 1 hour and then poured into water (1 L). The aqueous mixture was extracted with ether (3×300 mL), and the combined organic layers were washed with 2% sodium hydroxide aqueous solution (400 mL) and filtered through a layer of silica gel (40/60 prn). The filtrate was concentrated in vacuo to yield the title compound which was used without further purification.

Workup

  1. temperatureThe mixture was refluxed for 1 hour
  2. extractionThe aqueous mixture was extracted with ether (3×300 mL)
  3. washthe combined organic layers were washed with 2% sodium hydroxide aqueous solution (400 mL)
  4. filtrationfiltered through a layer of silica gel (40/60 prn)
  5. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-1d240826ff46495d8b47974c5b91930c
Source dataset
uspto-grants-2014_11
Patent number
US08895544B2

Reaction notes

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