Sodium Carbonate → 3-(4-Bromophenyl)pyridine

HRID 351748Notes

Reaction equation

HRID 351748 reaction equation
B1([C:7]2[CH:12]=[CH:11][CH:10]=[N:9][CH:8]=2)OCCCO1.[Br:13][C:14]1[CH:19]=[CH:18][C:17](I)=[CH:16][CH:15]=1.C(=O)([O-])[O-].[Na+].[Na+]>CN(C)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]>[Br:13][C:14]1[CH:19]=[CH:18][C:17]([C:7]2[CH:8]=[N:9][CH:10]=[CH:11][CH:12]=2)=[CH:16][CH:15]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 115221-Bromo-4-iodobenzeneHCID 41980053-(1,3,2-Dioxaborinan-2-yl)pyridine

Product 1

HCID 15152413-(4-Bromophenyl)pyridine

Reagents, catalysts & solvents 2

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

Conditions

Temperature
85 °C

Procedure

A mixture of pyridine-3-boronic acid 1,3-propanediol cyclic ester, 4-bromoiodobenzene (1.1 eq), [1,1 ′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (0.05 eq) and 2M aqueous sodium carbonate (5 eq) in N,N-dimethylformamide (2 ml/mmol) was stirred at 85° C. for 4 hours. After quenching with saturated aqueous ammonium chloride solution the mixture was partitioned between ethyl acetate and water and the crude product from the organic phase was chromatographed on silica gel eluting with a 1:9 mixture of ethyl acetate and hexane to afford the 3-(4-bromophenyl)pyridine compound as a solid.

Workup

  1. customAfter quenching with saturated aqueous ammonium chloride solution the mixture
  2. customwas partitioned between ethyl acetate and water
  3. customthe crude product from the organic phase was chromatographed on silica gel eluting with a 1:9 mixture of ethyl acetate and hexane

Sources & evidence

ORD record
ord-a4e1fa207e1643668eb120beddd09863
Source dataset
uspto-grants-2004_06
Patent number
US06743802B2

Reaction notes

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