Bromobenzene → HCID 25116096, compound

HRID 408661Notes

Reaction equation

HRID 408661 reaction equation
[CH3:1][C:2]1[CH:11]=[C:10]([N:12]2[CH2:16][CH2:15][CH:14]([NH2:17])[CH2:13]2)[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH:8]=2)[N:3]=1.Br[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C=CC=CC=2N(C)C)CCCCC1.CC(C)([O-])C.[Na+]>O.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].CCOCC.C1(C)C=CC=CC=1>[CH3:1][C:2]1[CH:11]=[C:10]([N:12]2[CH2:16][CH2:15][CH:14]([NH:17][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[CH2:13]2)[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH:8]=2)[N:3]=1

Participants

9

Reactant 4

HCID 7961BromobenzeneHCID 27342172-(Dicyclohexylphosphino)-2'-(dimethylamino)biphenylHCID 23676156Sodium t-butoxideHCID 68724556HCID 68724556, compound

Product 1

HCID 25116096HCID 25116096, compound

Reagents, catalysts & solvents 4

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 962WaterSolventHCID 1140TolueneSolventHCID 3283Diethyl EtherSolvent

Procedure

1-(2-Methyl-6-phenoxyquinolin-4-yl)pyrrolidin-3-ylamine (0.107 g; see Example 43 below), bromobenzene (0.058 g), 2-dicyclohexylphosphino-2′-dimethylaminobiphenyl (0.023 g), tris-(dibenzylideneacetone)dipalladium (0.03 g), sodium tert-butoxide (0.044 g) and toluene (3 mL) were heated in a microwave at 150° C. for 20 minutes. The reaction mixture was diluted with water and extracted with ethyl acetate, washed with water, dried (MgSO4), filtered and evaporated to give a brown oil. The residue was purified by chromatography on silica, eluting with a mixture of dichloromethane, and methanol. Evaporation of the desired fractions gave, after trituration with ether, the title compound as a white solid.

Workup

  1. extractionextracted with ethyl acetate
  2. washwashed with water
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customevaporated
  6. customto give a brown oil
  7. customThe residue was purified by chromatography on silica
  8. washeluting with a mixture of dichloromethane, and methanol
  9. customEvaporation of the desired fractions
  10. customgave

Sources & evidence

ORD record
ord-69cab92d28284ad383fdbbc088d62dcd
Source dataset
uspto-grants-2014_06
Patent number
US08759348B2

Reaction notes

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