Potassium Carbonate → HCID 59846238, compound

HRID 1697069Notes

Reaction equation

HRID 1697069 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](=[O:27])[CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([S:17]([N:20]2[CH2:25][CH2:24][N:23]([CH3:26])[CH2:22][CH2:21]2)(=[O:19])=[O:18])=[CH:13][CH:12]=1.C([O-])([O-])=O.[K+].[K+].I[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1>C(OCCCC)CCC.[Cu]>[CH3:26][N:23]1[CH2:22][CH2:21][N:20]([S:17]([C:14]2[CH:13]=[CH:12][C:11]([CH2:10][CH2:9][C:8]([C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=3[NH:1][C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)=[O:27])=[CH:16][CH:15]=2)(=[O:19])=[O:18])[CH2:25][CH2:24]1

Participants

6

Reactant 3

HCID 11430Potassium Carbonate2×HCID 11575Iodobenzene2×HCID 59846265HCID 59846265, compound

Product 1

HCID 59846238HCID 59846238, compound

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 8909Butyl etherSolvent

Conditions

Temperature
160 °C

Procedure

A mixture of 1-(2-aminophenyl)-3-[4-(4-methylpiperazine-1-sulfonyl)-phenyl]-propan-1-one (1.16 g), copper powder (90 mg), KI (19.7 mg), K2CO3 (495 mg) and iodobenzene (1.3 mL) in dibutyl ether (25 mL) was heated at 160° C. (oil bath temperature) overnight. A second aliquot of KI (19.7 mg), K2CO3 (495 mg) and iodobenzene (1.30 mL) was added, and the resulting mixture again heated at 160° C. overnight. The reaction mixture was then cooled and concentrated under reduced pressure. The residue was partitioned between water (50 mL) and EtOAc (50 mL), the organic layer separated, and the aqueous layer was extracted with EtOAc (2×50 mL). The combined organic extracts were washed with brine, dried over Na2SO4, filtered and evaporated under reduced pressure. The crude residue was purified by flash chromatography (DCM/MeOH, 98:2 for 5 minutes, 95:5 from minutes 10 to 15) to afford 3-[4-(4-methyl-piperazine-1-sulfonyl)-phenyl]-1-(2-phenylaminophenyl)-propan-1-one (258 mg). MS=464.0 [M+H]+.

Workup

  1. temperaturethe resulting mixture again heated at 160° C. overnight
  2. temperatureThe reaction mixture was then cooled
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was partitioned between water (50 mL) and EtOAc (50 mL)
  5. customthe organic layer separated
  6. extractionthe aqueous layer was extracted with EtOAc (2×50 mL)
  7. washThe combined organic extracts were washed with brine
  8. dry with materialdried over Na2SO4
  9. filtrationfiltered
  10. customevaporated under reduced pressure
  11. customThe crude residue was purified by flash chromatography (DCM/MeOH, 98:2 for 5 minutes, 95:5 from minutes 10 to 15)

Sources & evidence

ORD record
ord-92ecb27830df479a82aee8eb2cdb8e3e
Source dataset
uspto-grants-2012_04
Patent number
US08163906B2

Reaction notes

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