Sodium Carbonate → HCID 59162019, compound

HRID 216327Notes

Reaction equation

HRID 216327 reaction equation
[F:1][C:2]1[CH:7]=[C:6](B2OC(C)(C)C(C)(C)O2)[C:5]([F:17])=[CH:4][C:3]=1[C:18](=[O:20])[CH3:19].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:1][C:2]1[CH:7]=[C:6]([C:22]2[CH:27]=[CH:26][C:25]([F:28])=[CH:24][N:23]=2)[C:5]([F:17])=[CH:4][C:3]=1[C:18](=[O:20])[CH3:19]

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 27831712-Bromo-5-fluoropyridineHCID 68668352HCID 68668352, compound

Product 1

HCID 59162019HCID 59162019, compound

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolvent2×HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

Pd(dppf)Cl2 (579 mg, 0.7 mmol) was added to a degassed, ambient temperature solution of 1-[2,5-difluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]ethanone (2 g, 7.1 mmol), 2-bromo-5-fluoropyridine (2.5 g, 14 mmol) and sodium carbonate (2.26 g, 21 mmol) in N,N-dimethyformamide (20 mL) and water (10 mL). After heating at 80° C. overnight, the reaction mixture was poured into water and extracted with diethyl ether. The combined organic phases were dried (magnesium sulfate), filtered and concentrated in vacuo. Chromatography over silica eluting with 0-50% ethyl acetate/hexane afforded the title compound.

Workup

  1. extractionextracted with diethyl ether
  2. dry with materialThe combined organic phases were dried (magnesium sulfate)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0e0c1606d9ff47bc9ba2ff6114ed77f6
Source dataset
uspto-grants-2012_06
Patent number
US08193228B2

Reaction notes

Loading…