Cesium carbonate → Methyl 5-fluoromethoxypyridine-2-carboxylate

HRID 1842202Notes

Reaction equation

HRID 1842202 reaction equation
C1(C)C=CC(S(O[CH2:11][F:12])(=O)=O)=CC=1.[OH:14][C:15]1[CH:16]=[CH:17][C:18]([C:21]([O:23][CH3:24])=[O:22])=[N:19][CH:20]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[Cl-].[NH4+]>CN(C=O)C.C(OCC)(=O)C>[F:12][CH2:11][O:14][C:15]1[CH:16]=[CH:17][C:18]([C:21]([O:23][CH3:24])=[O:22])=[N:19][CH:20]=1

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 25517Ammonium ChlorideHCID 4715126Methyl 5-hydroxypyridine-2-carboxylateHCID 13862289Fluoromethyl 4-methylbenzenesulfonate

Product 1

HCID 57827265Methyl 5-fluoromethoxypyridine-2-carboxylateYield 42.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

A solution containing fluoromethyl toluene-4-sulfonate (233 mg) in DMF was added to a solution containing methyl 5-hydroxypyridine-2-carboxylate (100 mg) and cesium carbonate (532 mg) in DMF (5 mL). The reaction solution was stirred at 70° C. for three hours. The reaction solution was cooled to room temperature. Ethyl acetate and saturated aqueous ammonium chloride were added to the reaction solution, and the organic layer was separated. The organic layer was dried over anhydrous magnesium sulfate, and the insoluble matter was separated by filtration. The filtrate was concentrated and the residue was purified by silica gel column chromatography to obtain the title compound (51 mg).

Workup

  1. additionwas added to a solution
  2. temperatureThe reaction solution was cooled to room temperature
  3. customthe organic layer was separated
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. customthe insoluble matter was separated by filtration
  6. concentrationThe filtrate was concentrated
  7. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-cd0b9cac3bd340e4bb49e94532febaa3
Source dataset
uspto-grants-2015_02
Patent number
US08946210B2

Reaction notes

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