Potassium Carbonate → HCID 59287328, compound

HRID 2176847Notes

Reaction equation

HRID 2176847 reaction equation
Br[C:2]1[CH:7]=[C:6]([CH3:8])[N:5]=[C:4]([CH3:9])[CH:3]=1.[Br:10][C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][C:12]=1[F:18].C(=O)([O-])[O-].[K+].[K+]>CCOC(C)=O>[Br:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][C:2]2[CH:7]=[C:6]([CH3:8])[N:5]=[C:4]([CH3:9])[CH:3]=2)=[CH:13][C:12]=1[F:18]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 27791534-Bromo-3-fluorophenolHCID 130817354-Bromo-2,6-dimethylpyridine

Product 1

HCID 59287328HCID 59287328, compoundYield 73.8%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 4-bromo-2,6-dimethyl-pyridine (1 g, 5.4 mmol), 4-bromo-3-fluoro-phenol (0.59 g, 5.4 mmol), and potassium carbonate (0.89 g, 6.4 mmol) in xylenes (2 ml) was heated at 150° C. (oil bath temperature) in a sealed tube for 48 hours. After cooling to room temperature the mixture was diluted with EtOAc and filtered through a diatomaceous earth pad. The filtrate was evaporated till dryness and the crude product thus obtained was purified by column chromatography (silica gel; DCM to DCM/EtOAc up to 10% as eluent). The desired fractions were collected and evaporated in vacuo to yield intermediate 17 (1.18 g, 72%).

Workup

  1. temperatureAfter cooling to room temperature the mixture
  2. filtrationfiltered through a diatomaceous earth pad
  3. customThe filtrate was evaporated till dryness
  4. customthe crude product thus obtained
  5. customwas purified by column chromatography (silica gel; DCM to DCM/EtOAc up to 10% as eluent)
  6. customThe desired fractions were collected
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-9f310a2217ea4c70a0ab73ee85f10ecc
Source dataset
uspto-grants-2015_06
Patent number
US09067891B2

Reaction notes

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