Water → 2-Pyrazinecarboxylic acid, 5-(fluoromethoxy)-, methyl ester

HRID 1524630Notes

Reaction equation

HRID 1524630 reaction equation
C1(C)C=CC(S([O:10][CH2:11][F:12])(=O)=O)=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+].O[C:21]1[N:22]=[CH:23][C:24]([C:27]([O:29][CH3:30])=[O:28])=[N:25][CH:26]=1.O>CN(C=O)C>[F:12][CH2:11][O:10][C:21]1[N:22]=[CH:23][C:24]([C:27]([O:29][CH3:30])=[O:28])=[N:25][CH:26]=1

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 13862289Fluoromethyl 4-methylbenzenesulfonateHCID 178498852HCID 178498852, compound

Product 1

HCID 574756772-Pyrazinecarboxylic acid, 5-(fluoromethoxy)-, methyl esterYield 11.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

Fluoromethyl toluene-4-sulfonate (Journal of Labelled Compounds & Radiopharmaceuticals, 46 (6), 555-566; 2003) (344 mg) and cesium carbonate (824 mg) were added to a solution of methyl 5-hydroxypyrazine-2-carboxylate (130 mg) in DMF (2.0 mL). The reaction solution was stirred at 70° C. for 5 h and 30 min and then cooled to RT. Water was added to the reaction solution, followed by extraction with EtOAc. The organic layer was concentrated under reduced pressure. The residue was purified by NH-silica gel column chromatography to obtain the title compound (18.0 mg). 1H-NMR (400 MHz, CDCl3) δ (ppm): 4.03 (s, 3H), 6.14 (d, J=51.2 Hz, 2H), 8.42 (d, J=1.2 Hz, 1H), 8.94 (d, J=1.2 Hz, 1H).

Workup

  1. temperaturecooled to RT
  2. extractionfollowed by extraction with EtOAc
  3. concentrationThe organic layer was concentrated under reduced pressure
  4. customThe residue was purified by NH-silica gel column chromatography

Sources & evidence

ORD record
ord-d8d92d9823224417b71ac6a974b069fc
Source dataset
uspto-grants-2015_07
Patent number
US09079914B2

Reaction notes

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