Potassium Carbonate → HCID 57834979, compound

HRID 730583Notes

Reaction equation

HRID 730583 reaction equation
Br[C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4](=[O:20])[C:5](=[O:19])[N:6]2[CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[CH:13]=1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(C(C)C)=CC(C(C)C)=CC=2C(C)C)CCCCC1.C(=O)([O-])[O-].[K+].[K+].[C:61]([N:68]1[CH2:73][CH2:72][NH:71][CH2:70][CH2:69]1)([O:63][C:64]([CH3:67])([CH3:66])[CH3:65])=[O:62]>C(O)(C)(C)C.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[C:64]([O:63][C:61]([N:68]1[CH2:73][CH2:72][N:71]([C:2]2[CH:10]=[CH:9][CH:8]=[C:7]3[C:3]=2[C:4](=[O:20])[C:5](=[O:19])[N:6]3[CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[CH:13]=2)[CH2:70][CH2:69]1)=[O:62])([CH3:67])([CH3:65])[CH3:66]

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 143452tert-Butyl piperazine-1-carboxylateHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 284924774-Bromo-1-[(3-fluorophenyl)methyl]-1H-indole-2,3-dione

Product 1

HCID 57834979HCID 57834979, compoundYield 44.9%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 6386tert-ButanolSolvent

Conditions

Temperature
120 °C

Procedure

4-Bromo-1-(3-fluoro-benzyl)-1H-indole-2,3-dione (3.05 g) was dissolved in 45 mL of tert-butanol and Boc-piperazine (2.04 g), Pd2(dba)3 (164 mg), dicyclohexyl-(2′,4′,6′-triisopropyl-biphenyl-2-yl)-phosphane (217 mg), and potassium carbonate (1.84 g) were added. The mixture was stirred at 120° C. for 4 hours and then cooled to room temperature. The mixture was partitioned between ethyl acetate and water, and the organic layer was separated, dried over sodium sulfate and concentrated under reduced pressure. The residue was purified by chromatography to afford 1.80 g of 4-[1-(3-fluoro-benzyl)-2,3-dioxo-2,3-dihydro-1H-indol-4-yl]-piperazine-1-carboxylic acid tert-butyl ester. MS: 340 (M−Boc+H)+.

Workup

  1. temperaturecooled to room temperature
  2. customThe mixture was partitioned between ethyl acetate and water
  3. customthe organic layer was separated
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by chromatography

Sources & evidence

ORD record
ord-4a9c6682f9f64f8b9405a4ed8110ab7b
Source dataset
uspto-grants-2009_09
Patent number
US07582760B2

Reaction notes

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