Triethylamine → HCID 53715106, compound

HRID 2289167Notes

Reaction equation

HRID 2289167 reaction equation
Br[C:2]1[CH:3]=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.[C:12]([O:16][C:17](=[O:20])[CH:18]=[CH2:19])([CH3:15])([CH3:14])[CH3:13].C(N(CC)CC)C>C(#N)C.C(Cl)Cl.CC([O-])=O.CC([O-])=O.[Pd+2]>[C:12]([O:16][C:17](=[O:20])[CH:18]=[CH:19][C:2]1[CH:3]=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2)([CH3:15])([CH3:14])[CH3:13]

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 15458tert-Butyl acrylateHCID 214133-Bromoquinoline

Product 1

HCID 53715106HCID 53715106, compound

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 3-bromoquinoline 3-1(25 g, 120 mmol), acrylic acid tert-butyl ester (100 mL, 672 mmol), triethylamine (50 mL, 300 mmol) and Pd(OAc)2 (1.61 g, 7.2 mmol) in acetonitrile (100 mL) was refluxed for 18 hr. It is then cooled, diluted with 500 mL CH2Cl2 and filtered. The solution was washed with 10% NaHCO3, dried and concentrated. The residue was dissolved in 50 ml hot CH2Cl2 and diluted with 300 mL hexane. After standing, the desired product 3-2 was obtained as a crystalline compound.

Workup

  1. temperaturewas refluxed for 18 hr
  2. temperatureIt is then cooled
  3. filtrationfiltered
  4. washThe solution was washed with 10% NaHCO3
  5. customdried
  6. concentrationconcentrated
  7. dissolutionThe residue was dissolved in 50 ml hot CH2Cl2
  8. additiondiluted with 300 mL hexane

Sources & evidence

ORD record
ord-267b209d9d3644ed93066616648f4a78
Source dataset
uspto-grants-2000_07
Patent number
US06090944

Reaction notes

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