8-Aminoquinoline → HCID 57589728, compound

HRID 1783287Notes

Reaction equation

HRID 1783287 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.Br[C:13]1[CH:22]=[CH:21][C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:14]=1.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>[CH:19]1[C:20]2[C:15](=[CH:14][CH:13]=[CH:22][CH:21]=2)[CH:16]=[CH:17][C:18]=1[NH:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[NH:10][CH2:9][CH2:8][CH2:7]2

Participants

7

Reactant 3

HCID 113598-AminoquinolineHCID 113722-BromonaphthaleneHCID 23676156Sodium t-butoxide

Product 1

HCID 57589728HCID 57589728, compoundYield 52%

Reagents, catalysts & solvents 3

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

Procedure

To a flask equipped with a magnetic stirrer, reflux condensor, and nitrogen inlet was added 8-aminoquinoline (6.81 grams, 47.2 mmoles), 2-bromonapthalene (9.58 grams, 46.3 mmoles), tris(dibenzylideneacetone)dipalladium (0) (0.84 grams, 0.92 mmoles), rac-2,2′-bis(diphenylphosphino)-1,1′-binapthyl (0.6 grams, 0.92 mmoles), sodium tert-butoxide (8.86 grams, 92.2 mmoles) and anhydrous toluene (90 mL). The contents of the flask were refluxed for sixteen hours; cooled to room temperature; and filtered through a pad of silica gel. The silica gel pad was then eluted with dichloromethane (135 mL). The combined organic layers were concentrated in vacuo to yield a yellow solid. The solid was chromatographed on silica gel, eluting with a hexane/ethyl acetate gradient to afford 6.6 grams of the desired product as a yellow solid. 1H NMR (CDCl3) δ 8.75 (d, 1H), 8.4 (bs, 1H), 8.05 (d, 1H), 7.6-7.9 (m, 5H), 7.25-7.5 (m,5H), 7.2 (d, 1H).

Workup

  1. customTo a flask equipped with a magnetic stirrer
  2. temperaturereflux condensor, and nitrogen inlet
  3. temperatureThe contents of the flask were refluxed for sixteen hours
  4. filtrationand filtered through a pad of silica gel
  5. washThe silica gel pad was then eluted with dichloromethane (135 mL)
  6. concentrationThe combined organic layers were concentrated in vacuo
  7. customto yield a yellow solid
  8. customThe solid was chromatographed on silica gel
  9. washeluting with a hexane/ethyl acetate gradient

Sources & evidence

ORD record
ord-a5861cf62eb94184b8a6f8b14f7bdda8
Source dataset
uspto-grants-2009_03
Patent number
US07501386B2

Reaction notes

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