Water → HCID 68892581, compound

HRID 2220207Notes

Reaction equation

HRID 2220207 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5](I)=[C:6]([CH:21]=1)[CH2:7][N:8]([C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][C:13]=1[CH:19]=[CH2:20])[C:9](=[O:11])[CH3:10].CCN(CC)CC.O>CN(C=O)C.Cl[Pd]Cl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[CH:20]=[CH:19][C:13]3[CH:14]=[C:15]([Cl:18])[CH:16]=[CH:17][C:12]=3[N:8]([C:9](=[O:11])[CH3:10])[CH2:7][C:6]=2[CH:21]=1

Participants

6

Reactant 3

HCID 962WaterHCID 8471TriethylamineHCID 68892636N-(5-Bromo-2-iodo-benzyl)-N-(4-chloro-2-vinyl-phenyl)-acetamide

Product 1

HCID 68892581HCID 68892581, compoundYield 60%

Reagents, catalysts & solvents 2

HCID 24290Palladium ChlorideCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a stirred solution of N-(5-Bromo-2-iodo-benzyl)-N-(4-chloro-2-vinyl-phenyl)-acetamide (0.55 g, 1.5 mmol) and Et3N (0.63 mL, 4.5 mmol) in DMF (25 mL) was added PdCl2 (40 mg, 0.23 mmol) and the reaction was heated to 60° C. When the reaction was complete by HPLC the mixture was poured into H2O and extracted with Et2O. The Et2O layer was washed with H2O (2×20mL) and brine (20 mL), dried (MgSO4), filtered and concentrated in vacuo. The residue obtained was purified by flash chromatography eluting with CH2Cl2 to give 1-(8-Bromo-2-chloro-6H-dibenzo[b,f]azocin-5-yl)-ethanone (0.24 g, 60%).

Workup

  1. extractionextracted with Et2O
  2. washThe Et2O layer was washed with H2O (2×20mL) and brine (20 mL)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue obtained
  7. customwas purified by flash chromatography
  8. washeluting with CH2Cl2

Sources & evidence

ORD record
ord-f143519730fc43c5a73cab2ac466aa23
Source dataset
uspto-grants-2008_08
Patent number
US07417040B2

Reaction notes

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