HCID 68888601, compound → HCID 69734294, compound

HRID 1760601Notes

Reaction equation

HRID 1760601 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:21][CH:20]([CH3:22])[N:11]2[C:12]3[C:13](Br)=[CH:14][CH:15]=[CH:16][C:17]=3[CH:18]=[C:10]2[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Cu][C:24]#[N:25]>[C-]#N.C([N+](CC)(CC)CC)C.O1CCOCC1.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].C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][N:11]2[C:12]3[C:17]([CH2:18][C:24]#[N:25])=[CH:16][CH:15]=[CH:14][C:13]=3[CH:22]=[C:20]2[CH2:21]1)=[O:7])([CH3:3])([CH3:4])[CH3:2]

Participants

7

Reactant 2

HCID 68888601HCID 68888601, compoundHCID 178418546HCID 178418546, compound

Product 1

HCID 69734294HCID 69734294, compound

Reagents, catalysts & solvents 4

HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 3014735Tetraethylammonium cyanideCatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 312751,4-DioxaneSolvent

Procedure

A suspension of 0.30 g (0.82 mmol) 6-bromo-4-methyl-3,4-dihydro-1H-pyrazino[1,2-a]indole-2-carboxylic acid tert-butyl ester, 0.29 g (3.3 mmol) copper(I)cyanide, 34.0 mg (0.030 mmol) tris(dibenzylideneacetone)dipalladium(0), 72.9 mg (0.013 mmol) 1,1′-bis(diphenylphosphino)ferrocene and 128.3 mg (0.82 mmol) tetraethylammonium cyanide in 6 ml dioxane was heated under reflux for 18 h. The reaction mixture was filtered, diluted with ethyl acetate and extracted with 10% aqueous citric acid, 10% aqueous sodium bicarbonate solution and brine. After drying over magnesium sulfate and filtration, the solvent was removed at a rotary evaporator and the residue was purified by chromatography on silica gel (0.032-0.063 mm) with n-hexane:ethyl acetate (9:1) as eluant to give the product as a light yellow foam. ISP-MS: m/e 312.2 ([M+H+]).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 18 h
  3. filtrationThe reaction mixture was filtered
  4. additiondiluted with ethyl acetate
  5. extractionextracted with 10% aqueous citric acid, 10% aqueous sodium bicarbonate solution and brine
  6. dry with materialAfter drying over magnesium sulfate and filtration
  7. customthe solvent was removed at a rotary evaporator
  8. customthe residue was purified by chromatography on silica gel (0.032-0.063 mm) with n-hexane:ethyl acetate (9:1) as eluant

Sources & evidence

ORD record
ord-baec3b6681934827ac3e502ab4b2b968
Source dataset
uspto-grants-2005_01
Patent number
US06844345B2

Reaction notes

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