Cesium carbonate → HCID 58044104, compound

HRID 1918819Notes

Reaction equation

HRID 1918819 reaction equation
[NH2:1][CH2:2][CH2:3][N:4]1[C:12]2[CH2:11][CH2:10][CH2:9][CH2:8][C:7]=2[CH:6]=[C:5]1[C:13]([O:15]CC)=O.[C:18]([O:21][CH2:22][C:23]1[C:28]([Br:29])=[CH:27][CH:26]=[CH:25][C:24]=1Br)(=[O:20])[CH3:19].C([O-])([O-])=O.[Cs+].[Cs+]>[Cu]I.O1CCOCC1>[Br:29][C:28]1[CH:27]=[CH:26][CH:25]=[C:24]([N:1]2[CH2:2][CH2:3][N:4]3[C:12]4[CH2:11][CH2:10][CH2:9][CH2:8][C:7]=4[CH:6]=[C:5]3[C:13]2=[O:15])[C:23]=1[CH2:22][O:21][C:18](=[O:20])[CH3:19]

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 58043965Ethyl 1-(2-Aminoethyl)-4,5,6,7-tetrahydro-1H-indole-2-carboxylateHCID 592164132,6-Dibromobenzyl acetate

Product 1

HCID 58044104HCID 58044104, compoundYield 41.5%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
95 °C

Procedure

A 350-mL sealed tube equipped with a magnetic stirring bar was charged with 3,4,6,7,8,9-hexahydro-2H-pyrazino[1,2-a]indol-1-one 101k (5.0 g, 0.026 mol), 2,6-dibromobenzyl acetate 104g (16.2 g, 0.052 mol) N,N′-dimethylethylenediamine (2.6 mL, 0.026 mol), Cs2CO3 (17.0 g, 0.052 mol), and 1,4-dioxane (80 mL). After a stream of nitrogen was passed through the resulting suspension for 30 min., CuI (2.5 g, 0.013 mol) was added and the resulting reaction mixture was stirred at 95° C. for 16 h. Then the mixture was cooled to room temperature, partitioned between EtOAc (50 mL) and water (50 mL), and the organic phase was extracted with EtOAc (30 mL×3). The combined organic phases were washed with water (20 mL×2) and brine (20 mL×1), dried (Na2SO4), and concentrated. The crude product was purified by flash chromatography (dichloromethane:MeOH, 97:3) to give 35% yield (4.5 g) of 113a as white solids.

Workup

  1. customA 350-mL sealed tube
  2. customequipped with a magnetic stirring bar
  3. customthe resulting reaction mixture
  4. temperatureThen the mixture was cooled to room temperature
  5. custompartitioned between EtOAc (50 mL) and water (50 mL)
  6. extractionthe organic phase was extracted with EtOAc (30 mL×3)
  7. washThe combined organic phases were washed with water (20 mL×2) and brine (20 mL×1)
  8. dry with materialdried (Na2SO4)
  9. concentrationconcentrated
  10. customThe crude product was purified by flash chromatography (dichloromethane:MeOH, 97:3)

Sources & evidence

ORD record
ord-a78ce966521c442ca1b27379349188e4
Source dataset
uspto-grants-2013_12
Patent number
US08618107B2

Reaction notes

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