4-Bromopyridinium chloride → 4-(Furan-3-yl)pyridine

HRID 382134Notes

Reaction equation

HRID 382134 reaction equation
C1(C2C=CC=CC=2)[CH:6]=[CH:5][C:4]([C:7]2[CH:11]=[CH:10][O:9][CH:8]=2)=[CH:3][CH:2]=1.Cl.BrC1C=C[N:23]=CC=1.O1C=CC(B(O)O)=C1>>[O:9]1[CH:10]=[CH:11][C:7]([C:4]2[CH:5]=[CH:6][N:23]=[CH:2][CH:3]=2)=[CH:8]1

Participants

4

Reactant 3

HCID 881004-Bromopyridinium chlorideHCID 2734358Furan-3-boronic acidHCID 183802933-(Biphenyl-4-yl)furan

Product 1

HCID 108556024-(Furan-3-yl)pyridineYield 100%

Procedure

According to the procedure described in Example 1(a) for the preparation of 3-biphenyl-4-yl-furan, 4-bromopyridine hydrochloride (500 mg, 2.57 mmol) was coupled to fresh 3-furanboronic acid (see Thompson, W. J.; Gaudino, G. J. Org. Chem. 1984, 49, 5237-5243) to furnish 373 mg (100%) of crude 4-furan-3-yl-pyridine as an unstable solid that was used immediately. NMR and IR matched that of literature (see Ribereau, P.; Queguiner, G. Can. J. Chem. 1983, 61, 334-342 and Ishikura, M.; Ohta, T.; Terashima, M. Chem. Pharm. Bull. 1985, 33, 4755-4763).

Sources & evidence

ORD record
ord-8f263e51fdd943d29a054c5ba1b85a74
Source dataset
uspto-grants-2001_10
Patent number
US06306892B1

Reaction notes

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