Potassium Carbonate → HCID 22647912, compound

HRID 394143Notes

Reaction equation

HRID 394143 reaction equation
[Br:1][C:2]1[N:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[Cl:14])[C:5]([CH2:15][CH2:16][C:17]([NH:19][C:20]2[C:25]([Cl:26])=[CH:24][CH:23]=[CH:22][C:21]=2[Cl:27])=[O:18])=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.C([O-])(O)=O.[Na+].CCOC(C)=O.[Cu]I>[Br:1][C:2]1[CH:3]=[C:4]2[C:5]([CH2:15][CH2:16][C:17](=[O:18])[N:19]2[C:20]2[C:25]([Cl:26])=[CH:24][CH:23]=[CH:22][C:21]=2[Cl:27])=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[Cl:14])[N:7]=1

Participants

7

Reactant 2

HCID 11430Potassium CarbonateHCID 22647976HCID 22647976, compound

Product 1

HCID 22647912HCID 22647912, compound

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolventHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
155 °C

Procedure

To a suspension of 7.54 g of 3-[6-bromo-2-(2-chlorophenyl)pyridin-3-yl]-N-(2,6-dichlorophenyl)propanamide in 100 mL of DMF was added CuI (3.82 g) and powdered, dried K2CO3 (3.70 g). The mixture was heated to 155° C. for 30 min, then cooled and diluted with 250 mL of half-saturated NaHCO3 and 100 mL of EtOAc. The phases were separated and the aqueous phase was extracted 2×50 mL of EtOAc. The combined organics were washed with brine, dried (Na2SO4), and concentrated. The reside was purified by flash chromatography on a Biotage 65M column, eluting with a gradient system of 99:1 CH2Cl2-acetone to 97:3 CH2Cl2-acetone to yield the title compound as an off-white solid. Mass spectrum (ESI) 483 (M+1). 1H NMR (500 MHz, CDCl3): δ 2.72-2.92 (m, 3H); 2.96-3.06 (m, 1H); 6.37 (s, 1H); 7.39-7.54 (m. 2H); 7.56-7.60 (m, 2H).

Workup

  1. temperaturecooled
  2. customThe phases were separated
  3. extractionthe aqueous phase was extracted 2×50 mL of EtOAc
  4. washThe combined organics were washed with brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated
  7. customThe reside was purified by flash chromatography on a Biotage 65M column
  8. washeluting with a gradient system of 99:1 CH2Cl2-acetone to 97:3 CH2Cl2-acetone

Sources & evidence

ORD record
ord-cfe436e45c494294a2fb2a023aab15f3
Source dataset
uspto-grants-2004_10
Patent number
US06809199B2

Reaction notes

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