Dimethylformamide → HCID 86664267, compound

HRID 2387729Notes

Reaction equation

HRID 2387729 reaction equation
CN(C=O)C.[Cl:6][C:7]1[C:12]([OH:13])=[CH:11][C:10]([F:14])=[CH:9][N:8]=1.[OH-].[Na+].[CH3:17][O:18][CH2:19]Cl>O.C(OCC)C>[Cl:6][C:7]1[C:12]([O:13][CH2:17][O:18][CH3:19])=[CH:11][C:10]([F:14])=[CH:9][N:8]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 7864Chloromethyl Methyl EtherHCID 14798Sodium HydroxideHCID 242292052-Chloro-5-fluoropyridin-3-ol

Product 1

HCID 86664267HCID 86664267, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

A DMF (10 ml) solution of 2-chloro-5-fluoro-3-hydroxypyridine (500 mg) was cooled to 0° C. Sodium hydroxide (60% oil dispersion: 149 mg) was added to the reaction solution, and the obtained mixture was stirred at 0° C. for 15 minutes. Chloromethyl methyl ether (293 ul) was added to the reaction solution at the same temperature as described above, and the obtained mixture was heated to room temperature and stirred for 1 hour. Diethyl ether and water were added to the reaction solution, and the organic layer was successively washed with water and a saturated sodium chloride aqueous solution. The organic layer was dried over anhydrous magnesium sulfate and then filtered. The filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (n-heptane:ethyl acetate=19:1 to 7:3), so as to obtain the title compound (598 mg).

Workup

  1. temperaturewas heated to room temperature
  2. stirringstirred for 1 hour
  3. washthe organic layer was successively washed with water
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (n-heptane:ethyl acetate=19:1 to 7:3)

Sources & evidence

ORD record
ord-ada3c6d870714d2caf2a30bb7b917a69
Source dataset
uspto-grants-2012_09
Patent number
US08268848B2

Reaction notes

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