Cesium carbonate → Methyl 5-fluoromethoxypyridine-2-carboxylate

HRID 1524632Notes

Reaction equation

HRID 1524632 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+].[NH4+].[Cl-]>CN(C=O)C.CCOC(C)=O>[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-carboxylate

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 3 h. The reaction solution was cooled to RT. EtOAc and saturated aqueous NH4Cl were added to the reaction solution, and the organic layer was separated. The organic layer was dried over anhydrous MgSO4, and the insoluble matter was separated by filtration.

Workup

  1. additionwas added to a solution
  2. temperatureThe reaction solution was cooled to RT
  3. customthe organic layer was separated
  4. dry with materialThe organic layer was dried over anhydrous MgSO4
  5. customthe insoluble matter was separated by filtration

Sources & evidence

ORD record
ord-ae65763f67ab4127a3d6c3b7e535a246
Source dataset
uspto-grants-2015_07
Patent number
US09079914B2

Reaction notes

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