3-Nitrophenylboronic Acid → 4-(3-nitrophenyl)pyridine

HRID 2086800Notes

Reaction equation

Cl.Br[C:3]1[CH:8]=[CH:7][N:6]=[CH:5][CH:4]=1.C(=O)(O)[O-].[Na+].OB(O)[C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([N+:22]([O-:24])=[O:23])[CH:17]=1>C1(C)C=CC=CC=1.CO.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>[N+:22]([C:18]1[CH:17]=[C:16]([C:3]2[CH:8]=[CH:7][N:6]=[CH:5][CH:4]=2)[CH:21]=[CH:20][CH:19]=1)([O-:24])=[O:23]

Participants

Conditions

Temperature: 80 °C

Procedure

To a mixture of 4-bromopyridine hydrochloride (5.25 g) and tetrakis(triphenylphosphine)palladium(0) (0.93 g) in toluene (50 ml) was added 3M aqueous solution of sodium bicarbonate (27 ml) and a solution of dihydroxy(3-nitrophenyl)borane (5.0 g) in methanol (12 ml). The mixture was stirred at 80° C. for 1 hour and cooled. Then the mixture was poured into aqueous sodium bicarbonate and extracted with ethyl acetate twice. The combined organic phase was washed with aqueous sodium bicarbonate and brine, dried over magnesium sulfate and concentrated. The residue was chromatographed on silica gel (1%-2% methanol in chloroform) to give 4-(3-nitrophenyl)pyridine (3.46 g).

Workup

temperaturecooled
extractionextracted with ethyl acetate twice
washThe combined organic phase was washed with aqueous sodium bicarbonate and brine
dry with materialdried over magnesium sulfate
concentrationconcentrated
customThe residue was chromatographed on silica gel (1%-2% methanol in chloroform)

Sources & evidence

ORD record: ord-4eef49a063fc4c8ea76e1c5f7f29992f
Source dataset: uspto-grants-2004_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06727245B2

Reaction notes

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