Water → HCID 22329559, compound

HRID 586323Notes

Reaction equation

HRID 586323 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][N:3]=1.[F:9][C:10]1[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][C:11]=1B1OC(C)(C)C(C)(C)O1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].O>O1CCOCC1.C1C=CC([PH+]([C]2[CH][CH][CH][CH]2)C2C=CC=CC=2)=CC=1.C1C=CC([PH+]([C]2[CH][CH][CH][CH]2)C2C=CC=CC=2)=CC=1.C(Cl)Cl.Cl[Pd]Cl.[Fe]>[F:8][C:5]1[CH:6]=[CH:7][C:2]([C:11]2[CH:12]=[C:13]([N+:16]([O-:18])=[O:17])[CH:14]=[CH:15][C:10]=2[F:9])=[N:3][CH:4]=1

Participants

7

Reactant 4

HCID 962WaterHCID 62657Potassium Phosphate, TribasicHCID 27831712-Bromo-5-fluoropyridineHCID 38332972-Fluoro-5-nitrophenylboronic acid, pinacol ester

Product 1

HCID 22329559HCID 22329559, compoundYield 48.7%

Reagents, catalysts & solvents 2

HCID 53485975CID 53485975CatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

To a degassed mixture of 2-bromo-5-fluoropyridine (1.88 g, 10.7 mmol), 2-(2-fluoro-5-nitrophenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane (3.13 g, 11.6 mmol) and potassium phosphate (8.2 g, 38.6 mmol) in 1,4-dioxane (40 ml) was added dichloro[1,1′-bis(diphenylphosphino)ferrocene]-palladium(II) dichloromethane adduct (189 mg) and the mixture stirred for 24 h at 90° C. The reaction was cooled to ambient temperature, poured into water (100 ml) and extracted with ethyl acetate (4×50 ml). The combined organic phases were dried over anhydrous sodium sulfate, filtered and evaporated to dryness. Purification by chromatography (silica gel, CH2Cl2) and then crystallisation from isohexane gave 5-fluoro-2-(2-fluoro-5-nitrophenyl)pyridine (1.23 g, 44%): MS (ES+) m/z 237.

Workup

  1. temperatureThe reaction was cooled to ambient temperature
  2. extractionextracted with ethyl acetate (4×50 ml)
  3. dry with materialThe combined organic phases were dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. customevaporated to dryness
  6. customPurification by chromatography (silica gel, CH2Cl2)
  7. customcrystallisation from isohexane

Sources & evidence

ORD record
ord-9ab99393939c493695c9c04f98e3ed26
Source dataset
uspto-grants-2005_08
Patent number
US06936608B2

Reaction notes

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