HCID 14621980, compound → HCID 15099588, compound

HRID 2295201Notes

Reaction equation

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

Participants

Conditions

Temperature: -78 °C

Procedure

A solution of 3-(2,2-dibromoethenyl)-4-(4-fluorophenyl)-2-(1-methylethyl)-6-phenylpyridine (2.105 gm, 4.43 mmol) in dry THF (23 ml) was cooled to -78° C. and treated with n-BuLi (1.5M in hexane, 5.95 ml, 8.93 mmol) over a 4 minute period. After stirring at -78° C. for 1.25 hours, the deep purple solution was quenched with saturated NH4Cl, warmed to room temperature, diluted with H2O, and extracted 2× with Et2 O. The combined Et2O extracts were 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 3-ethynyl-4-(4-fluorophenyl)-2-(1-methylethyl)-6-phenylpyridine as white needles. The mother liquor was stripped and recrystallized again from hot hexane to give additional product (total yield 1.199 gm, 86%)

Workup

customthe deep purple solution was quenched with saturated NH4Cl
temperaturewarmed to room temperature
additiondiluted with H2O
extractionextracted 2× with Et2 O
washThe combined Et2O extracts were 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-55ab601fa072456c9cf45b412f067ddb
Source dataset: uspto-grants-1997_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05691322

Reaction notes

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