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Sodium Carbonate → 2,2,2-Trifluoro-1-[4-(5-fluoropyridin-2-yl)phenyl]ethanone

HRID 216334
Notes
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Reaction equation

HRID 216334 reaction equation
[F:1][C:2]([F:21])([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:23]1[CH:28]=[CH:27][C:26]([F:29])=[CH:25][N:24]=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:21][C:2]([F:1])([F:20])[C:3]([C:5]1[CH:6]=[CH:7][C:8]([C:23]2[CH:28]=[CH:27][C:26]([F:29])=[CH:25][N:24]=2)=[CH:9][CH:10]=1)=[O:4]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 27831712-Bromo-5-fluoropyridineHCID 569730602,2,2-Trifluoro-1-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]ethan-1-one

Product 1

HCID 591619282,2,2-Trifluoro-1-[4-(5-fluoropyridin-2-yl)phenyl]ethanone

Reagents, catalysts & solvents 3

HCID 44119782
Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)
Catalyst
HCID 962WaterSolvent
HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

Pd(dppf)Cl2 (2.5 g, 3.3 mmol) was added to a degassed, ambient temperature solution of 2,2,2-trifluoro-1-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]ethanone (20 g, 67 mmol), 2-bromo-5-fluoropyridine (11.6 g, 67 mmol) and sodium carbonate (12.7 g, 134 mmol) in N,N-dimethylformamide (4400 mL) and water (90 mL). After heating at 90° C. overnight, the reaction mixture was poured into ice (400 g) 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. extractionextracted with diethyl ether
  2. dry with materialThe combined organic extracts were dried (magnesium sulfate)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b30d3b8e4fcc46e4a25fd3fdda072028
Source dataset
uspto-grants-2012_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08193228B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes