Sodium Carbonate → HCID 59161939, compound

HRID 216335Notes

Reaction equation

HRID 216335 reaction equation
[F:1][CH:2]([F:20])[C:3]([C:5]1[CH:10]=[CH:9][C:8](B2OC(C)(C)C(C)(C)O2)=[CH:7][CH:6]=1)=[O:4].Br[C:22]1[CH:27]=[CH:26][C:25]([F:28])=[CH:24][N:23]=1.C(=O)([O-])[O-].[Na+].[Na+]>CN(C)C=O.O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[F:20][CH:2]([F:1])[C:3]([C:5]1[CH:6]=[CH:7][C:8]([C:22]2[CH:27]=[CH:26][C:25]([F:28])=[CH:24][N:23]=2)=[CH:9][CH:10]=1)=[O:4]

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 27831712-Bromo-5-fluoropyridineHCID 866384901022154-90-0

Product 1

HCID 59161939HCID 59161939, compound

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

Pd(dppf)Cl2 (3.06 g, 4.2 mmol) was added to a degassed, ambient temperature solution of 2,2-difluoro-1-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]ethanone (30 g, 84 mmol), 2-bromo-5-fluoropyridine (15 g, 84 mmol) and sodium carbonate (20 g, 189 mmol) in N,N-dimethylformamide (400 mL) and H2O (100 mL). After stirring at 90° C. overnight, the reaction mixture was poured into ice and extracted with diethyl ether. The combined organic extracts were dried (magnesium sulfate), filtered and concentrated in vacuo. Chromatography over silica eluting with petroleum ether/ethyl acetate (20:1) afforded the title compound.

Workup

  1. additionthe reaction mixture was poured into ice
  2. extractionextracted with diethyl ether
  3. dry with materialThe combined organic extracts were dried (magnesium sulfate)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-54e886e50d2b4c25a568e3c72414680c
Source dataset
uspto-grants-2012_06
Patent number
US08193228B2

Reaction notes

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