Sodium Carbonate → 2-Hydroxy-5-phenylpyridine

HRID 1747785Notes

Reaction equation

Br[C:2]1[CH:3]=[CH:4][C:5](=[O:8])[NH: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+]>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.C1(C)C=CC=CC=1>[C:9]1([C:2]2[CH:3]=[CH:4][C:5](=[O:8])[NH:6][CH:7]=2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 5-bromopyridin-2(1H)-one (500 mg), phenylboronic acid (385 mg), tetrakis(triphenylphosphine)palladium(0) (498 mg), 2M aqueous sodium carbonate solution (2.87 mL) and toluene (7.0 mL) was stirred at 100° C. for 1 hr under microwave irradiation. The reaction mixture was cooled to room temperature, and filtered through celite. To the filtrate was added saturated aqueous sodium hydrogen carbonate solution, and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (100 mg).

Workup

temperatureThe reaction mixture was cooled to room temperature
filtrationfiltered through celite
additionTo the filtrate was added saturated aqueous sodium hydrogen carbonate solution
extractionthe mixture was extracted with ethyl acetate
dry with materialThe extract was dried over anhydrous sodium sulfate
concentrationconcentrated under reduced pressure
customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record: ord-4fb81f2c2c0b42e19516b2eededd690f
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09150588B2

Reaction notes

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