Sodium Carbonate → HCID 46314930, compound

HRID 639710Notes

Reaction equation

HRID 639710 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([F:8])=[N:6][CH:7]=1.[C:9]1(B(O)O)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.C(O)C.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[F:8][C:5]1[CH:4]=[CH:3][C:2]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:7][N:6]=1

Participants

8

Reactant 3

HCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 27831685-Bromo-2-fluoropyridine

Product 1

HCID 46314930HCID 46314930, compoundYield 93.6%

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

To a solution of 5-bromo-2-fluoropyridine (2.33 g, 13.2 mmol) in toluene (100 mL) and ethanol (25 mL) were added Pd(PPh3)4 (764 mg, 0.66 mmol), phenylboronic acid (2.42 g, 19.8 mmol, 1.5 eq) and a solution of sodium carbonate (9.6 g, 90.7 mmol, 6.85 eq) in water (50 mL). The reaction mixture was heated to 90 C for 2 hours, allowed to cool to room temperature and partitioned between water and ethyl acetate. The organic layer was dried and evaporated and the residue purified by column chromatography (petrol/ethyl acetate gradient) to afford the title compound as a colorless oil (2.14 g, 93%)

Workup

  1. temperatureThe reaction mixture was heated to 90 C for 2 hours
  2. custompartitioned between water and ethyl acetate
  3. customThe organic layer was dried
  4. customevaporated
  5. customthe residue purified by column chromatography (petrol/ethyl acetate gradient)

Sources & evidence

ORD record
ord-6ca0eb62c3c445d1b30d89697f2a7f42
Source dataset
uspto-grants-2010_04
Patent number
US07691885B2

Reaction notes

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