3-Bromoquinoline → HCID 18518589, compound

HRID 1369112Notes

Reaction equation

HRID 1369112 reaction equation
Br[C:2]1[CH:3]=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.[Li]CCCC.[CH2:17]([N:19]([CH2:34][CH3:35])[CH2:20][CH2:21][N:22]1[C:32]2[C:27](=[C:28]([Br:33])[CH:29]=[CH:30][CH:31]=2)[C:25](=[O:26])[C:23]1=[O:24])[CH3:18].[NH4+].[Cl-]>CCOCC>[CH2:34]([N:19]([CH2:17][CH3:18])[CH2:20][CH2:21][N:22]1[C:32]2[C:27](=[C:28]([Br:33])[CH:29]=[CH:30][CH:31]=2)[C:25]([OH:26])([C:2]2[CH:3]=[N:4][C:5]3[C:10]([CH:11]=2)=[CH:9][CH:8]=[CH:7][CH:6]=3)[C:23]1=[O:24])[CH3:35]

Participants

6

Reactant 4

HCID 214133-BromoquinolineHCID 25517Ammonium ChlorideHCID 10958318HCID 10958318, compoundHCID 178418339Butyllithium

Product 1

HCID 18518589HCID 18518589, compoundYield 5%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To 3-bromoquinoline (56.3 mg, 1.1 eq) in anhydrous Et2O (1.0 mL) at −50° C. (internal temperature) and under a nitrogen atmosphere was added n-BuLi (0.18 mL, 1.1 eq, 1.53 M in hexanes). Stirring was continued for minutes and then to the resulting red/brown coloured precipitate was added 1-(2-diethylaminoethyl)-4-bromoisatin (80.0 mg, 2.46×10−4 mol) in anhydrous Et2O (2.0 mL) and the resulting dark blue coloured mixture was stirred for a further 8.5 hours at −50° C. Saturated aqueous NH4Cl (1.5 mL) was added and the mixture was allowed to warm to room temperature. The mixture was extracted with EtOAc and the combined extracts were dried (anhydrous Na2SO4). After filtration, the solvent was removed in vacuo. Purification was carried out by flash chromatography (silica gel, eluting 2% MeOH in CHCl3) to yield the title compound as a yellow oil (5.3 mg, 5%).

Workup

  1. waitwas continued for minutes
  2. stirringwas stirred for a further 8.5 hours at −50° C
  3. extractionThe mixture was extracted with EtOAc
  4. dry with materialthe combined extracts were dried (anhydrous Na2SO4)
  5. filtrationAfter filtration
  6. customthe solvent was removed in vacuo
  7. customPurification
  8. washwas carried out by flash chromatography (silica gel, eluting 2% MeOH in CHCl3)

Sources & evidence

ORD record
ord-157c585c01b44a1ab5387b68daf7f644
Source dataset
uspto-grants-2003_06
Patent number
US06576656B1

Reaction notes

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