Potassium Carbonate → HCID 59846162, compound

HRID 1697064Notes

Reaction equation

HRID 1697064 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9](=[O:28])[CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][C:15]([S:18]([N:21]2[CH2:26][CH2:25][N:24]([CH3:27])[CH2:23][CH2:22]2)(=[O:20])=[O:19])=[CH:14][CH:13]=1.C([O-])([O-])=O.[K+].[K+].I[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1>C(OCCCC)CCC.[Cu]>[Cl:8][C:6]1[CH:5]=[CH:4][C:3]([C:9](=[O:28])[CH2:10][CH2:11][C:12]2[CH:13]=[CH:14][C:15]([S:18]([N:21]3[CH2:26][CH2:25][N:24]([CH3:27])[CH2:23][CH2:22]3)(=[O:20])=[O:19])=[CH:16][CH:17]=2)=[C:2]([NH:1][C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[CH:7]=1

Participants

6

Reactant 3

HCID 11430Potassium Carbonate2×HCID 11575Iodobenzene2×HCID 59846224HCID 59846224, compound

Product 1

HCID 59846162HCID 59846162, compoundYield 68%

Reagents, catalysts & solvents 2

HCID 23978CopperCatalyst2×HCID 8909Butyl etherSolvent

Conditions

Temperature
160 °C

Procedure

A mixture of 1-(2-amino-4-chlorophenyl)-3-[4-(4-methylpiperazine-1-sulfonyl)-phenyl]-propan-1-one (1.268 g), copper powder (38 mg), KI (99 mg), K2CO3 (829 mg) and iodobenzene (1.35 mL) in dibutyl ether (25 mL) was heated to 160° C. (oil bath temperature) overnight. Additional copper powder (38 mg), KI (99 mg), K2CO3 (829 mg) and iodobenzene (1.35 mL) were added, and the resulting mixture was again stirred at 160° C. overnight. The reaction mixture was then cooled and concentrated under reduced pressure. The residue was partitioned between water and EtOAc, the organic layer was separated, and the aqueous layer was extracted 2× with EtOAc (50 mL). The combined organic extracts were washed with brine, dried over anhydrous Na2SO4, filtered, and evaporated under reduced pressure. The crude residue was purified by flash chromatography (DCM/MeOH, 100/0 for 5 minutes, 98/2 from minute 8 to 20) to give 1-(4-chloro-2-phenylaminophenyl)-3-[4-(4-methylpiperazine-1-sulfonyl)-phenyl]-propan-1-one (1.02 g; 68% yield). MS=498.0 [M+H]+.

Workup

  1. temperatureThe reaction mixture was then cooled
  2. concentrationconcentrated under reduced pressure
  3. customThe residue was partitioned between water and EtOAc
  4. customthe organic layer was separated
  5. extractionthe aqueous layer was extracted 2× with EtOAc (50 mL)
  6. washThe combined organic extracts were washed with brine
  7. dry with materialdried over anhydrous Na2SO4
  8. filtrationfiltered
  9. customevaporated under reduced pressure
  10. customThe crude residue was purified by flash chromatography (DCM/MeOH, 100/0 for 5 minutes, 98/2 from minute 8 to 20)

Sources & evidence

ORD record
ord-a91fa6e6bbae44138d8672b3787058fd
Source dataset
uspto-grants-2012_04
Patent number
US08163906B2

Reaction notes

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