HCID 15099566, compound → HCID 15099591, compound

HRID 1720729Notes

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-(4fluorophenyl)-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-271c7fd923a446d591d9f0cd46e31139
Source dataset: uspto-grants-1996_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05506219

Reaction notes

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