Potassium Carbonate → HCID 55138372, compound

HRID 1175149Notes

Reaction equation

HRID 1175149 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][N:3]=1.[F:9][C:10]1[CH:15]=[C:14]([F:16])[CH:13]=[CH:12][C:11]=1[OH:17].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[Br:8][C:5]1[CH:6]=[CH:7][C:2]([O:17][C:11]2[CH:12]=[CH:13][C:14]([F:16])=[CH:15][C:10]=2[F:9])=[N:3][CH:4]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 693532,5-DibromopyridineHCID 1230512,4-Difluorophenol

Product 1

HCID 55138372HCID 55138372, compoundYield 91.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2,5-Dibromopyridine (3.0 g; 12.66 mmol), 2,4-difluorophenol (4.11 g; 31.65 mmol) and K2CO3 (5.25 g; 38 mmol) in DMF (40 ml) are stirred at 150° C. for 3 hours. The reaction mixture is poured on water and extracted with TBME three times. The combined organic phases are dried over Na2SO4, filtered, evaporated to dryness and purified via chromatography (SiO2, heptane/TBME 97:3) to yield the title compound as white crystals (3.3 g; 85%). MS (m/z) ES+: 286, 288 (MH+). Retention time: 3.05 minutes (LC-MS method 2).

Workup

  1. additionThe reaction mixture is poured on water
  2. extractionextracted with TBME three times
  3. dry with materialThe combined organic phases are dried over Na2SO4
  4. filtrationfiltered
  5. customevaporated to dryness
  6. custompurified via chromatography (SiO2, heptane/TBME 97:3)

Sources & evidence

ORD record
ord-27014c3b56184e3da1aea8fa8bf7c1ad
Source dataset
uspto-grants-2010_11
Patent number
US07838674B2

Reaction notes

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