8-Aminoquinoline → HCID 57589732, compound

HRID 1783285Notes

Reaction equation

HRID 1783285 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[CH:7]2.[C:12]([C:16]1[CH:21]=[CH:20][C:19](Br)=[CH:18][CH:17]=1)([CH3:15])([CH3:14])[CH3:13].CC(C)([O-])C.[Na+]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1(P(C2C=CC=CC=2)C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(C)C=CC=CC=1>[C:12]([C:16]1[CH:21]=[CH:20][C:19]([NH:1][C:2]2[CH:3]=[CH:4][CH:5]=[C:6]3[C:11]=2[NH:10][CH2:9][CH2:8][CH2:7]3)=[CH:18][CH:17]=1)([CH3:15])([CH3:14])[CH3:13]

Participants

7

Reactant 3

HCID 113598-AminoquinolineHCID 775951-Bromo-4-tert-butylbenzeneHCID 23676156Sodium t-butoxide

Product 1

HCID 57589732HCID 57589732, compoundYield 82%

Reagents, catalysts & solvents 3

HCID 634876Binap, (A+-)-CatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent

Procedure

To a flask equipped with a magnetic stirrer, reflux condenser, and nitrogen inlet was added 8-aminoquinoline (14.4 grams, 0.10 moles), 4-tert-butyl bromobenzene (21.3 grams, 0.10 moles), tris(dibenzylideneacetone)dipalladium (0) (1.8 grams, 0.002 moles), rac-2,2′-bis(diphenylphosphino)-1,1′-binapthyl (2.5 grams, 0.004 moles), sodium tert-butoxide (19.4 grams, 0.20 moles) and anhydrous toluene (150 mL). The contents of the flask were refluxed for four days; cooled to room temperature; and filtered through a pad of silica gel. The silica gel pad was then eluted with dichloromethane (240 mL). The combined organic layers were concentrated in vacuo to yield a dark blue solid. The solid was chromatographed on silica gel, eluting with hexane/ethyl acetate (20:1) to afford 23 grams of the desired product as a yellow solid. 1H NMR (CDCl3) δ 8.8 (m, 1H), 8.2 (bs, 1H), 8.1 (d, 1H), 7.1-7.5 (m, 9H), 1.35 (s, 9H).

Workup

  1. customTo a flask equipped with a magnetic stirrer
  2. temperaturereflux condenser, and nitrogen inlet
  3. temperatureThe contents of the flask were refluxed for four days
  4. filtrationand filtered through a pad of silica gel
  5. washThe silica gel pad was then eluted with dichloromethane (240 mL)
  6. concentrationThe combined organic layers were concentrated in vacuo
  7. customto yield a dark blue solid
  8. customThe solid was chromatographed on silica gel
  9. washeluting with hexane/ethyl acetate (20:1)

Sources & evidence

ORD record
ord-801f1dbefbd2482bb4cff0e1cae83ede
Source dataset
uspto-grants-2009_03
Patent number
US07501386B2

Reaction notes

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