Triethylamine → HCID 11231942, compound

HRID 2217840Notes

Reaction equation

HRID 2217840 reaction equation
Br[C:2]1[C:11]([Cl:12])=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2.[CH:13]1(CN)C[CH2:17][CH2:16][CH2:15][CH2:14]1.C([N:23]([CH2:26]C)[CH2:24][CH3:25])C.[C]=[O:29]>CN1CCCC1=O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[Cl:12][C:11]1[CH:10]=[CH:9][C:8]2[N:7]=[CH:6][CH:5]=[CH:4][C:3]=2[C:2]=1[C:26]([NH:23][CH2:24][CH:25]1[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1)=[O:29]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 76688CyclohexanemethylamineHCID 2181616416560-60-4HCID 178418416HCID 178418416, compound

Product 1

HCID 11231942HCID 11231942, compound

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

To a solution of 5-bromo-6-chloroquinoline (prepared according to the method of Journal of Heterocyclic Chemistry 1967, 4, 410) (4.0 g), cyclohexanemethylamine (4.2 mL) and triethylamine (2.4 mL) in N-methylpyrrolidinone (40 mL) was added dichlorobis(triphenylphosphine)palladium(II) (1.6 g). The mixture was heated with stirring at 100° C. under a 6 bar pressure of carbon monoxide for 18 hours after which it was cooled and filtered through diatomaceous earth, washing with methanol. The combined organics were concentrated to give a residue which was purified (SiO2, isohexane:ethyl acetate:ammonia in methanol (7 M) 49:49:2 as eluant) to yield the title compound as a solid (4.6 g).

Workup

  1. temperatureThe mixture was heated
  2. temperaturewas cooled
  3. filtrationfiltered through diatomaceous earth
  4. washwashing with methanol
  5. concentrationThe combined organics were concentrated
  6. customto give a residue which
  7. customwas purified (SiO2, isohexane:ethyl acetate:ammonia in methanol (7 M) 49:49:2 as eluant)

Sources & evidence

ORD record
ord-d25765e24f4c4b059b9b1b21571b74cf
Source dataset
uspto-grants-2008_08
Patent number
US07408065B2

Reaction notes

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