Ethanol → 4-(4-Bromo-3-fluorophenyl)pyridine

HRID 2065468Notes

Reaction equation

HRID 2065468 reaction equation
C(=O)([O-])[O-].[Na+].[Na+].O.[N:8]1[CH:13]=[CH:12][C:11](B(O)O)=[CH:10][CH:9]=1.[Br:17][C:18]1[CH:23]=[CH:22][C:21](I)=[CH:20][C:19]=1[F:25].C1(C)C=CC=CC=1.C(O)C>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Br:17][C:18]1[CH:23]=[CH:22][C:21]([C:11]2[CH:12]=[CH:13][N:8]=[CH:9][CH:10]=2)=[CH:20][C:19]=1[F:25]

Participants

8

Reactant 6

HCID 702EthanolHCID 962WaterHCID 1140TolueneHCID 10340Sodium CarbonateHCID 27250061-Bromo-2-fluoro-4-iodobenzeneHCID 2734379(Pyridin-4-yl)boronic acid

Product 1

HCID 666841274-(4-Bromo-3-fluorophenyl)pyridine

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Procedure

Sodium carbonate (0.86 g, 0.0081 mol) in water (3.0 mL, 0.17 mol) was added to a mixture of 4-pyridinylboronic acid (0.5 g, 0.004 mol), 1-bromo-2-fluoro-4-iodobenzene (1.5 g, 0.0049 mol), and tetrakis(triphenylphosphine)palladium(0) (0.02 g, 0.00002 mol) in toluene (6.0 mL, 0.056 mol) and ethanol (3.0 mL, 0.051 mol). The resulting mixture was irradiated by microwave at 120° C. for 30 min. The reaction mixture was extracted with EtOAc and the combined organic layers were dried over Na2SO4, filtered, and concented in-vacuo. The residue was purified by CombiFlash (EtOAc in hexanes: 40%) to afford the desired product.

Workup

  1. customThe resulting mixture was irradiated by microwave at 120° C. for 30 min
  2. extractionThe reaction mixture was extracted with EtOAc
  3. dry with materialthe combined organic layers were dried over Na2SO4
  4. filtrationfiltered
  5. customThe residue was purified by CombiFlash (EtOAc in hexanes: 40%)

Sources & evidence

ORD record
ord-117c9ae461d041d5b8badc8cbc0c10e4
Source dataset
uspto-grants-2012_10
Patent number
US08288417B2

Reaction notes

Loading…