HCID 21471314, compound → HCID 21471459, compound

HRID 1720722Notes

Reaction equation

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

Participants

Conditions

Temperature: -78 °C

Procedure

A solution of 3-(2,2-Dibromoethenyl)-4-(4-fluorophenyl)-2-(1-methylethyl)quinoline (25.2 mmol) in dry THF (140 ml) was cooled to -78° C. and treated with n-BuLi (1.6M in hexane, 33 ml, 52.8 mmol) over a 1 minute period. After stirring at -78° C. for one hour, the dark brown solution was quenched with saturated NH4Cl, warmed to room temperature, diluted with H2O, and extracted with Et2O. The Et2O extract was washed with brine, dried (Na2SO4), filtered and stripped to give a yellow oil. The oil was boiled in hot hexane and cooled (-15° C.) to afford 3-Ethynyl-4-(4-fluorophenyl)-2-(1-methylethyl)-quinoline (5.198 gm) as yellow crystals. The mother liquor was stripped and chromatographed (flash, Merck SiO2, 4% EtOAc in hexane) to afford additional product which was recrystallized from hot hexane. A total of 6.793 gm (93%) of 3-Ethynyl-4-(4-fluorophenyl)-2-(1-methylethyl)quinoline was obtained.

Workup

customthe dark brown solution was quenched with saturated NH4Cl
temperaturewarmed to room temperature
additiondiluted with H2O
extractionextracted with Et2O
extractionThe Et2O extract
washwas washed with brine
dry with materialdried (Na2SO4)
filtrationfiltered
customto give a yellow oil
temperaturecooled (-15° C.)

Sources & evidence

ORD record: ord-546e5f8efa4b4cdea88f1f4838793e69
Source dataset: uspto-grants-1996_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05506219

Reaction notes

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