HCID 21471327, compound → HCID 11066164, compound

HRID 1720715Notes

Reaction equation

HRID 1720715 reaction equation
Br[C:2](Br)=[CH:3][C:4]1[C:5]([C:17]2[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=2)=[N:6][C:7]2[C:12]([C:13]=1[CH:14]([CH3:16])[CH3:15])=[CH:11][CH:10]=[CH:9][CH:8]=2.[Li]CCCC>C1COCC1>[C:3]([C:4]1[C:5]([C:17]2[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=2)=[N:6][C:7]2[C:12]([C:13]=1[CH:14]([CH3:16])[CH3:15])=[CH:11][CH:10]=[CH:9][CH:8]=2)#[CH:2]

Participants

4

Reactant 2

HCID 21471327HCID 21471327, compoundHCID 178418339Butyllithium

Product 1

HCID 11066164HCID 11066164, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

A solution of 3-(2,2-dibromoethenyl)-2-(4-fluorophenyl)-4-(1-methylethyl)quinoline (2.563 gm, 5.71 mmol) in dry THF (30 ml) was cooled to -78° C. and treated with n-BuLi (1.5M in hexane, 8.0 ml, 12 mmol) over a 5 minute period. After stirring at -78° C. for 1.25 hours, the brown solution was quenched with saturated NH4Cl, warmed to room temperature, diluted with H2O, and extracted 2× with Et2O. The combined Et2O extracts were washed with brine, dried (Na2SO4), filtered and stripped to give a yellow solid. The solid was recrystallized from hot hexane to afford analytically pure 3-ethynyl-2-(4-fluorophenyl)-4-(1-methylethyl)quinoline as off-white crystals (1.205 gm, 73%).

Workup

  1. customthe brown solution was quenched with saturated NH4Cl
  2. temperaturewarmed to room temperature
  3. additiondiluted with H2O
  4. extractionextracted 2× with Et2O
  5. washThe combined Et2O extracts were washed with brine
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. customto give a yellow solid
  9. customThe solid was recrystallized from hot hexane

Sources & evidence

ORD record
ord-c5c034749e2f48c8b6dcfcdb86709fdb
Source dataset
uspto-grants-1996_04
Patent number
US05506219

Reaction notes

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