Potassium Carbonate → HCID 20824954, compound

HRID 1760594Notes

Reaction equation

HRID 1760594 reaction equation
Br[C:2]1[C:10]2[N:9]3[C@H:11]([CH3:16])[CH2:12][NH:13][C:14](=[O:15])[C:8]3=[CH:7][C:6]=2[CH:5]=[C:4]([F:17])[CH:3]=1.[C:18](=O)([O-])[O-].[K+].[K+].CB1OB(C)OB(C)O1>CN(C)C=O>[F:17][C:4]1[CH:3]=[C:2]([CH3:18])[C:10]2[N:9]3[C@H:11]([CH3:16])[CH2:12][NH:13][C:14](=[O:15])[C:8]3=[CH:7][C:6]=2[CH:5]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 574072TrimethylboroxineHCID 68892787HCID 68892787, compound

Product 1

HCID 20824954HCID 20824954, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

1.2 g (R)-6-bromo-8-fluoro-4-methyl-3,4-dihydro-2H-pyrazino[1,2-a]indol-1-one was dissolved in 12 ml N,N-dimethylformamide under argon. 0.45 gTetrakis-(triphenylphosphine)palladium, 1.56 g potassium carbonate and 0.55 ml trimethylboroxine were added. The mixture was heated overnight at 110° C., allowed to cool to room temperature, filtered over dicalite and washed through with tetrahydrofuran. The solvents were evaporated under reduced pressure and the residue purified by column chromatography on silica gel (1:1 to 1:3 toluene/ethyl acetate) to afford the title product as an off-white solid. Yield: 300 mg ISP-MS: m/e 233.1 ([M+H]+).

Workup

  1. temperatureto cool to room temperature
  2. filtrationfiltered over dicalite
  3. washwashed through with tetrahydrofuran
  4. customThe solvents were evaporated under reduced pressure
  5. customthe residue purified by column chromatography on silica gel (1:1 to 1:3 toluene/ethyl acetate)

Sources & evidence

ORD record
ord-a07d5b80db8a4bb9bf8280c09503658c
Source dataset
uspto-grants-2005_01
Patent number
US06844345B2

Reaction notes

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