HCID 15099566, compound → HCID 15099591, compound

HRID 2295220Notes

Reaction equation

Br[C:2](Br)=[CH:3][C:4]1[C:5]([C:19]2[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=2)=[N:6][C:7]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:8][C:9]=1[CH:10]([CH3:12])[CH3:11].[Li]CCCC>C1COCC1>[C:3]([C:4]1[C:5]([C:19]2[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=2)=[N:6][C:7]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:8][C:9]=1[CH:10]([CH3:12])[CH3:11])#[CH:2]

Participants

Conditions

Temperature: -78 °C

Procedure

A solution of 3-(2,2-Dibromoethenyl)-2-(4-fluorophenyl)-4-(1-methylethyl)-6-phenylpyridine (2.677 gm, 5.63 mmol) in dry THF (25 ml) was cooled to -78° C. and treated with n-BuLi (1.6M in hexane, 7.75 ml, 12.4 mmol) over a 1 minute period. After stirring at -78° C. for one hours, the deep green solution was quenched with saturated NH4Cl, warmed to room temperature, diluted with H2O, and extracted once with Et2O. The Et2O extract was washed with brine, dried (Na2SO4), filtered and stripped to give a yellow solid. The solid was recrystallized from a minimum amount of hot hexane to afford analytically pure 3-Ethynyl-2-(4-fluorophenyl)-4-(1-methylethyl)-6-phenylpyridine as yellow crystals (1.572 gm, 89%).

Workup

customthe deep green solution was quenched with saturated NH4Cl
temperaturewarmed to room temperature
additiondiluted with H2O
extractionextracted once with Et2O
extractionThe Et2O extract
washwas washed with brine
dry with materialdried (Na2SO4)
filtrationfiltered
customto give a yellow solid
customThe solid was recrystallized from a minimum amount of hot hexane

Sources & evidence

ORD record: ord-b8a80f2d424146e1a1837bb63e177b10
Source dataset: uspto-grants-1997_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05691322

Reaction notes

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