Butanal → HCID 71284792, compound

HRID 1481748Notes

Reaction equation

HRID 1481748 reaction equation
Br[C:2]1[CH:10]=[CH:9][C:8]2[N:7]3[CH2:11][CH2:12][N:13]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:14][C:6]3=[CH:5][C:4]=2[CH:3]=1.CN(C=O)C.N1CCCC1.[CH:32](=[O:36])[CH2:33][CH2:34][CH3:35]>CCOC(C)=O.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].C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1>[C:32]([C:2]1[CH:10]=[CH:9][C:8]2[N:7]3[CH2:11][CH2:12][N:13]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:14][C:6]3=[CH:5][C:4]=2[CH:3]=1)(=[O:36])[CH2:33][CH2:34][CH3:35]

Participants

8

Reactant 4

HCID 261ButanalHCID 6228DimethylformamideHCID 31268PyrrolidineHCID 712847451,1-Dimethylethyl 8-bromo-3,4-dihydropyrazino[1,2-a]indole-2(1H)-carboxylate

Product 1

HCID 71284792HCID 71284792, compoundYield 73%

Reagents, catalysts & solvents 3

HCID 634876Binap, (A+-)-CatalystHCID 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladiumCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
115 °C

Procedure

To a vial was added tert-butyl 8-bromo-3,4-dihydropyrazino[1,2-a]indole-2(1H)-carboxylate (1.4 g, 4.0 mmol), Pd(dba)2 (75 mg, 2 mol %), BINAP (75 mg, 3 mol %), and crushed 4 Å MS (2.0 g). The vial was evacuated and backfilled under argon. To the vial was then added DMF (15 mL), pyrrolidine (660 μL, 8.0 mmol), and butyraldehyde (1.0 mL, 12 mmol). The vial was then sealed under argon and heated to 115° C. for 6 h. The reaction mixture was then cooled to room temperature, diluted with EtOAc (50 mL), and filtered through celite. The filtrate was washed with H2O (50 mL) and brine (50 mL). The organic layer was dried over Na2SO4, filtered, and concentrated to afford a crude residue that was purified on silica gel (1:1 hexanes/EtOAc) to afford the title compound as a white solid (1.0 g, 73%).

Workup

  1. customcrushed 4 Å MS (2.0 g)
  2. customThe vial was evacuated
  3. customThe vial was then sealed under argon
  4. temperatureThe reaction mixture was then cooled to room temperature
  5. filtrationfiltered through celite
  6. washThe filtrate was washed with H2O (50 mL) and brine (50 mL)
  7. dry with materialThe organic layer was dried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customto afford a crude residue that
  11. customwas purified on silica gel (1:1 hexanes/EtOAc)

Sources & evidence

ORD record
ord-fe37c7dc42b44f2c9067944d3ddc7b26
Source dataset
uspto-grants-2016_08
Patent number
US09409905B2

Reaction notes

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