Sodium Carbonate → 3-(4-Bromophenyl)pyridine

HRID 1839151Notes

Reaction equation

HRID 1839151 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
  2. customthe mixture was 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-61966a2d664447b69039edbdec026a3c
Source dataset
uspto-grants-2004_01
Patent number
US06677351B2

Reaction notes

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