Potassium Carbonate → HCID 22647989, compound

HRID 394169Notes

Reaction equation

HRID 394169 reaction equation
Br[C:2]1[CH:7]=[C:6]([Br:8])[N:5]=[C:4]([C:9]2[CH:14]=[CH:13][C:12]([F:15])=[CH:11][C:10]=2[F:16])[C:3]=1[CH2:17][CH2:18][C:19]([NH:21][C:22]1[C:27]([Cl:28])=[CH:26][CH:25]=[CH:24][C:23]=1[Cl:29])=[O:20].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.C(=O)(O)[O-].[Na+].[Cu](I)I>[Br:8][C:6]1[CH:7]=[C:2]2[C:3]([CH2:17][CH2:18][C:19](=[O:20])[N:21]2[C:22]2[C:27]([Cl:28])=[CH:26][CH:25]=[CH:24][C:23]=2[Cl:29])=[C:4]([C:9]2[CH:14]=[CH:13][C:12]([F:15])=[CH:11][C:10]=2[F:16])[N:5]=1

Participants

6

Reactant 2

HCID 11430Potassium CarbonateHCID 22648099HCID 22648099, compound

Product 1

HCID 22647989HCID 22647989, compound

Reagents, catalysts & solvents 3

HCID 83717Copper iodideCatalystHCID 6228DimethylformamideSolventHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
155 °C

Procedure

To a solution of 3-[4,6-dibromo-2-(2,4-difluorophenyl)pyridin-3-yl]-N-(2,6-dichlorophenyl)propanamide (1 g) in 30 mL of DMF was added potassium carbonate (0.489 g) and copper iodide (0.5 g). The reaction mixture was stirred for 24 h at 155° C., then cooled and diluted with 10 mL of saturated sodium bicarbonate. This solution was extracted twice with 10 mL of ethyl acetate, washed with 10 mL of brine, dried with sodium sulfate, then concentrated. The residue was purified by flash chromatography with 1% acetone in CH2Cl2. Mass spectrum m/z (ESI) 485.3 (M+1).

Workup

  1. temperaturecooled
  2. extractionThis solution was extracted twice with 10 mL of ethyl acetate
  3. washwashed with 10 mL of brine
  4. dry with materialdried with sodium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by flash chromatography with 1% acetone in CH2Cl2

Sources & evidence

ORD record
ord-ffcec20c67bd4b2b8b4499b7a4f5b813
Source dataset
uspto-grants-2004_10
Patent number
US06809199B2

Reaction notes

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