Water → HCID 22473534, compound

HRID 2183974Notes

Reaction equation

HRID 2183974 reaction equation
Cl[C:2]1[CH:7]=[N:6][CH:5]=[CH:4][N:3]=1.[F:8][C:9]1[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][C:10]=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:9]1[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][C:10]=1[C:2]1[CH:7]=[N:6][CH:5]=[CH:4][N:3]=1

Participants

7

Reactant 4

HCID 962WaterHCID 62657Potassium Phosphate, TribasicHCID 73277ChloropyrazineHCID 38332972-Fluoro-5-nitrophenylboronic acid, pinacol ester

Product 1

HCID 22473534HCID 22473534, compound

Reagents, catalysts & solvents 2

HCID 53485975CID 53485975CatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

To a degassed mixture of 2-chloropyrazine (1.01 g, 8 mmol), 2-(2-fluoro-5-nitrophenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane (2.36 g, 8.84 mmol) and potassium phosphate (6.3 g, 30 mmol) in 1,4-dioxane (30 ml) was added dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium(II) dichloromethane adduct (0.11 g) and the mixture stirred for 15 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 on silica gel eluting with 50% dichloromethane in isohexane then ethyl acetate gave 2-(2-fluoro-5-nitrophenyl)pyrazine: m/z (ES+) 220 (M++H).

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 on silica gel eluting with 50% dichloromethane in isohexane

Sources & evidence

ORD record
ord-9ae564b482ac4e399f48f2ef73b1f6bc
Source dataset
uspto-grants-2005_05
Patent number
US06900215B2

Reaction notes

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