Potassium Carbonate → HCID 57722976, compound

HRID 1987027Notes

Reaction equation

HRID 1987027 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9](=[O:22])[CH2:10][CH2:11][C:12]1[C:17](Br)=[CH:16][C:15]([O:19][CH3:20])=[CH:14][C:13]=1[Br:21].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.[Cu]I>[Br:21][C:13]1[CH:14]=[C:15]([O:19][CH3:20])[CH:16]=[C:17]2[C:12]=1[CH2:11][CH2:10][C:9](=[O:22])[N:8]2[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[Cl:1]

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 57722992HCID 57722992, compound

Product 1

HCID 57722976HCID 57722976, compoundYield 62.3%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6228DimethylformamideSolvent

Procedure

N-(2-chlorophenyl)-3-(2,6-dibromo-4-methoxyphenyl)propanamide (1.40 g, 3.128 mmol), copper(I) iodide (0.895 g, 4.694 mmol), and potassium carbonate (0.865 g, 6.259 mmol) in DMF (15 ml), were heated under reflux for 30 min., cooled and evaporated in vacuo. The residue was treated with 2M hydrochloric acid (80 ml) and extracted with dichloromethane (2×50 ml). The extracts were passed through a hydrophobic frit, evaporated in vacuo and the residue purified by flash chromatography over silica (50 g) eluting with cyclohexane-ethyl acetate gradient (100:0-50:50) to give the product as a white solid (0.714 g, 62%)

Workup

  1. temperatureunder reflux for 30 min.
  2. temperaturecooled
  3. customevaporated in vacuo
  4. additionThe residue was treated with 2M hydrochloric acid (80 ml)
  5. extractionextracted with dichloromethane (2×50 ml)
  6. customevaporated in vacuo
  7. customthe residue purified by flash chromatography over silica (50 g)
  8. washeluting with cyclohexane-ethyl acetate gradient (100:0-50:50)

Sources & evidence

ORD record
ord-4938c0329629481892706b74c94459d7
Source dataset
uspto-grants-2009_06
Patent number
US07550480B2

Reaction notes

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