Water → HCID 68890106, compound

HRID 1760595Notes

Reaction equation

HRID 1760595 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(=O)([O-])[O-].[Cs+].[Cs+].[CH2:24](B(CC)CC)[CH3:25].O>CN(C)C=O.O1CCCC1>[CH2:24]([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)[CH3:25]

Participants

7

Reactant 4

HCID 962WaterHCID 7357TriethylboraneHCID 10796Cesium carbonateHCID 68892787HCID 68892787, compound

Product 1

HCID 68890106HCID 68890106, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

6.2 g (R)-6-bromo-8-fluoro-4-methyl-3,4-dihydro-2H-pyrazino[1,2-a]indol-1-one was dissolved in 150 ml N,N-dimethylformamide under argon. 1.43 g (Dppf)PdCl2, 39 g caesium carbonate and 41.6 ml of a 1M solution of triethylborane in tetrahydrofuran were added. The mixture was heated 15 h at 50° C., allowed to cool to room temperature and poured into water. The aqueous mixture was extracted with ethyl acetate. The combined organic phases washed with brine, dried over magnesium sulfate and evaporated. The residue was purified by column chromatography on reversed phase silica gel (6:4 to 3:7 water/methanol) to afford the title product as an off-white solid. Yield: 1.8 g. ISP-MS: m/e 247.3 ([M+H]+).

Workup

  1. temperatureto cool to room temperature
  2. extractionThe aqueous mixture was extracted with ethyl acetate
  3. washThe combined organic phases washed with brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated
  6. customThe residue was purified by column chromatography on reversed phase silica gel (6:4 to 3:7 water/methanol)

Sources & evidence

ORD record
ord-21a5b670cafa4c47995b3485e844f46e
Source dataset
uspto-grants-2005_01
Patent number
US06844345B2

Reaction notes

Loading…