Potassium Carbonate → HCID 10933825, compound

HRID 1696696Notes

Reaction equation

HRID 1696696 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][SH:10])=[CH:5][CH:4]=1.[F-].[K+].C(=O)([O-])[O-].[K+].[K+].Br[C:20]1[C:25]([OH:26])=[CH:24][CH:23]=[CH:22][N:21]=1>C(OCC)(=O)C.CN(C=O)C>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][S:10][C:20]2[C:25]([OH:26])=[CH:24][CH:23]=[CH:22][N:21]=2)=[CH:5][CH:4]=1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 230702-Bromo-3-pyridinolHCID 804074-Methoxy-alpha-toluenethiolHCID 522689Potassium Fluoride

Product 1

HCID 10933825HCID 10933825, compoundYield 43%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
150 °C

Procedure

4-Methoxy-α-toluenethiol (9.4 mL), potassium fluoride (3.34 g) and potassium carbonate (10.3 g) were added to a DMF (100 mL) solution of 2-bromo-3-hydroxypyridine (10 g, 57.5 mmol), and stirred at 150° C. for 3 days. The reaction liquid was diluted with ethyl acetate, and washed three times with distilled water. The organic layer was dried with magnesium sulfate, and concentrated under reduced pressure. The obtained residue was crystallized from ethyl acetate and hexane to obtain the intended compound (6.2 g, 43%) as a white solid.

Workup

  1. customThe reaction liquid
  2. washwashed three times with distilled water
  3. dry with materialThe organic layer was dried with magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe obtained residue was crystallized from ethyl acetate and hexane

Sources & evidence

ORD record
ord-1f41b7ffa76e4b9d8f9afe36911961d6
Source dataset
uspto-grants-2012_04
Patent number
US08163770B2

Reaction notes

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