Cesium carbonate → HCID 69421686, compound

HRID 1292706Notes

Reaction equation

HRID 1292706 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2.Br[C:13]1[CH:22]=[CH:21][C:16]([C:17]([O:19][CH3:20])=[O:18])=[CH:15][CH:14]=1.C([O-])([O-])=O.[Cs+].[Cs+].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.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]>[CH3:20][O:19][C:17](=[O:18])[C:16]1[CH:21]=[CH:22][C:13]([NH:1][C:2]2[CH:11]=[CH:10][CH:9]=[C:8]3[C:3]=2[CH:4]=[CH:5][CH:6]=[N:7]3)=[CH:14][CH:15]=1

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 119115-Aminoquinoline2×HCID 12081Methyl 4-bromobenzoateHCID 634876Binap, (A+-)-

Product 1

HCID 69421686HCID 69421686, compound

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

5-Aminoquinoline (14.4 g, 0.10 mol), methyl 4-bromobenzoate (21.6 g, 0.10 mol), Cs2CO3 (45.6 g, 0.14 mol), rac-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (0.96 g, 1.5 mmol) and tris(dibenzylideneacetone)dipalladium (0) (0.44 g, 0.5 mmol) were mixed in toluene (15 ml) and stirred at 100° C. for 170 h. At the end of this time the reaction mixture was screened and the filtrates were evaporated under reduced pressure. The resultant residue was purified by column chromatography on silica gel eluting with a (1:1) mixture of hexane and ethyl acetate. The elute was collected and the solvent was removed under reduced pressure to yield the product (contaminated with a small amount of 5-aminoquinoline) which was used in the next stage without further purification.

Workup

  1. customthe filtrates were evaporated under reduced pressure
  2. customThe resultant residue was purified by column chromatography on silica gel eluting with a (1:1) mixture of hexane and ethyl acetate
  3. customThe elute was collected
  4. customthe solvent was removed under reduced pressure
  5. customto yield the product (
  6. customwas used in the next stage without further purification

Sources & evidence

ORD record
ord-d12591d15be74bd6a6f1daa05c001b54
Source dataset
uspto-grants-2007_07
Patent number
US07238228B2

Reaction notes

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