Iodine → HCID 67291168, compound

HRID 1685401Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][CH:3]=1.[Mg].II.[C:15]([C:17]1[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][N:18]=1)#N.S(=O)(=O)(O)[OH:25]>C1COCC1>[OH:23][C:20]1[CH:21]=[CH:22][C:17]([C:15]([C:2]2[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][CH:3]=2)=[O:25])=[N:18][CH:19]=1

Participants

Conditions

Temperature: 10 °C

Procedure

A solution of 23.4 g (104 mM) of 1-bromo-4-trifluoromethylbenzene in 100 ml of THF is added dropwise to 2.53 g (104 mM) of magnesium metal and one crystal of iodine covered with 100 ml of THF. The mixture is stirred at the reflux temperature of the solvent for 2 hours and then cooled to 10° C. A solution of 5 g (42 mM) of 2-cyano-5-pyridinol in 80 ml of THF is then added dropwise. The mixture is refluxed for 2 hours and then stirred for 18 h at room temperature. It is treated with 120 ml of 0.5 N sulfuric acid and the solvents are evaporated off under reduced pressure. The medium is brought to neutral pH by washing with saturated sodium bicarbonate solution, extraction is carried out with ethyl acetate and the extract is dried over magnesium sulfate. After purification by chromatography on silica gel (eluent: toluene/ethyl acetate 8/2, then pure ethyl acetate and finally ethyl acetate/aqueous ammonia 95/5; v/v), the expected product is obtained in the form of a pale pink solid with a yield of 66%.

Workup

temperatureThe mixture is refluxed for 2 hours
stirringstirred for 18 h at room temperature
customthe solvents are evaporated off under reduced pressure
washby washing with saturated sodium bicarbonate solution, extraction
dry with materialthe extract is dried over magnesium sulfate
customAfter purification by chromatography on silica gel (eluent

Sources & evidence

ORD record: ord-dcf0a10fa9344a67bb266172f95aa1a4
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08148407B2

Reaction notes

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