Potassium Carbonate → HCID 10253075, compound

HRID 1987023Notes

Reaction equation

HRID 1987023 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9](=[O:27])[CH2:10][CH2:11][C:12]1[C:13]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[Cl:26])=[N:14][C:15]([Br:19])=[CH:16][C:17]=1Br.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.[Cu]I>[Br:19][C:15]1[CH:16]=[C:17]2[C:12]([CH2:11][CH2:10][C:9](=[O:27])[N:8]2[C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[Cl:1])=[C:13]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[Cl:26])[N:14]=1

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 57722994HCID 57722994, compound

Product 1

HCID 10253075HCID 10253075, compoundYield 51%

Reagents, catalysts & solvents 2

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

Procedure

N-(2-Chlorophenyl)-3-[4,6-dibromo-2-(2-chlorophenyl)-3-pyridinyl]propanamide (942 mg, 1.78 mmol) was divided into six portions and each dissolved in DMF (3 ml), and treated with potassium carbonate (50 mg, 0.362 mmol) and copper(I) iodide (15 mg, 0.079 mmol), and heated in a Smith Creator microwave at 180° for 15 min. All reactions were then combined and evaporated in vacuo. The residue was treated with water (15 ml) and extracted with dichloromethane (2×20 ml). The extracts were passed through a hydrophobic frit and evaporated in vacuo. The residue was purified by column chromatography over silica (20 g) eluting with a cyclohexane-ethyl acetate gradient (100:0-0:100). (70:30) gave the product as a white foam (406 mg, 51%).

Workup

  1. temperatureheated in a Smith Creator microwave at 180° for 15 min
  2. customevaporated in vacuo
  3. additionThe residue was treated with water (15 ml)
  4. extractionextracted with dichloromethane (2×20 ml)
  5. customevaporated in vacuo
  6. customThe residue was purified by column chromatography over silica (20 g)
  7. washeluting with a cyclohexane-ethyl acetate gradient (100:0-0:100)

Sources & evidence

ORD record
ord-d19aa987bc2e40ab83c693674b4f4f9e
Source dataset
uspto-grants-2009_06
Patent number
US07550480B2

Reaction notes

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