Sodium Carbonate → HCID 59161960, compound

HRID 216340Notes

Reaction equation

HRID 216340 reaction equation
[F:1][CH:2]([F:21])[C:3]([C:5]1[CH:10]=[CH:9][C:8](B2OC(C)(C)C(C)(C)O2)=[CH:7][C:6]=1[F:20])=[O:4].Br[C:23]1[CH:28]=[CH:27][C:26]([F:29])=[CH:25][N:24]=1.C([O-])([O-])=O.[Na+].[Na+]>CN(C=O)C.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:21][CH:2]([F:1])[C:3]([C:5]1[CH:10]=[CH:9][C:8]([C:23]2[CH:28]=[CH:27][C:26]([F:29])=[CH:25][N:24]=2)=[CH:7][C:6]=1[F:20])=[O:4]

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 27831712-Bromo-5-fluoropyridineHCID 86638493HCID 86638493, compound

Product 1

HCID 59161960HCID 59161960, 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

A mixture of 2,2-difluoro-1-[2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]ethanone (21 g, 70 mmol), 2-bromo-5-fluoropyridine (12.32 g, 70 mmol), Na2CO3 (14.84 g, 140 mmol) in DMF (300 mL) and H2O (80 mL) was degassed and filled with nitrogen. Then Pd(dppf)Cl2 (2.56 g, 3.5 mmol) was added and the mixture was again degassed and filled with nitrogen. After stirring overnight at 90° C., the reaction mixture was poured into ice (80 g) and extracted with Et2O (500 mL×3). The combined extracts were dried (MgSO4), filtered and concentrated, and the residue was purified by column chromatography (PE/EA 20:1) to give the title compound.

Workup

  1. customwas degassed
  2. additionfilled with nitrogen
  3. customthe mixture was again degassed
  4. additionfilled with nitrogen
  5. additionthe reaction mixture was poured into ice (80 g)
  6. extractionextracted with Et2O (500 mL×3)
  7. dry with materialThe combined extracts were dried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customthe residue was purified by column chromatography (PE/EA 20:1)

Sources & evidence

ORD record
ord-4579284031bb4b17b968fa740e34b7ae
Source dataset
uspto-grants-2012_06
Patent number
US08193228B2

Reaction notes

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