Sodium Carbonate → 4-(4-Bromo-3-fluorophenyl)pyridine

HRID 2035681Notes

Reaction equation

HRID 2035681 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5](I)=[CH:4][C:3]=1[F:9].[N:10]1[CH:15]=[CH:14][C:13](B(O)O)=[CH:12][CH:11]=1.C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1.O.O.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:1][C:2]1[CH:7]=[CH:6][C:5]([C:13]2[CH:14]=[CH:15][N:10]=[CH:11][CH:12]=2)=[CH:4][C:3]=1[F:9]

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 27250061-Bromo-2-fluoro-4-iodobenzeneHCID 2734379(Pyridin-4-yl)boronic acid

Product 1

HCID 666841274-(4-Bromo-3-fluorophenyl)pyridineYield 21.9%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 218864351,4-Dioxane--water (1/1)Solvent

Procedure

1-Bromo-2-fluoro-4-iodobenzene (300 mg, 0.997 mmol), 4-pyridineboronic acid (147 mg, 1.196 mmol), Na2CO3(211 mg, 1.994 mmol) and tetrakis(triphenylphosphine)palladium (230 mg, 0.199 mmol) in 3.3 mL of 1:1 Dioxane/water were heated to 100° C. for 20 h. The reaction was slowly warmed to room temperature, diluted with water and extracted with EtOAc. The organic phase was separated, dried (Na2SO4) and evaporated to dryness, giving an oil. This material was chromatographed on silica gel, eluting with 0-10% ethyl acetate in hexanes to give 4-(4-bromo-3-fluorophenyl)pyridine (55 mg) as an off-white solid.

Workup

  1. extractionextracted with EtOAc
  2. customThe organic phase was separated
  3. dry with materialdried (Na2SO4)
  4. customevaporated to dryness
  5. customgiving an oil
  6. customThis material was chromatographed on silica gel
  7. washeluting with 0-10% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-85a9374533824e999933f3cbaee06000
Source dataset
uspto-grants-2013_11
Patent number
US08575150B2

Reaction notes

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