Cesium carbonate → HCID 24985118, compound

HRID 913383Notes

Reaction equation

HRID 913383 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][C:8]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:7]2)([O-:3])=[O:2].C([O-])([O-])=O.[Cs+].[Cs+].Br[CH2:25][CH:26]1[CH2:28][CH2:27]1>CC#N>[CH:26]1([CH2:25][N:9]2[C:10]3[C:6](=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:12][CH:11]=3)[CH:7]=[C:8]2[C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH2:28][CH2:27]1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 81503BromomethylcyclopropaneHCID 280312Ethyl 5-nitro-1H-indole-2-carboxylate

Product 1

HCID 24985118HCID 24985118, compoundYield 68.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
90 °C

Procedure

To a suspension of commercially available ethyl 5-nitro-1H-indole-2-carboxylate (0.5 g, 2.13 mmol) in MeCN (7 mL) was added Cs2CO3 (1.39 g, 4.27 mmol) and (bromomethyl)cyclopropane (0.58 g, 4.27 mmol). The mixture was heated at 90° C., under N2, for 5 h. Upon cooling, the mixture was concentrated in vacuo and partitioned between EtOAc and H2O. The organic phase was washed with sat'd brine, dried (Na2SO4) and concentrated in vacuo. The residue was purified by flash chromatography (0-30% EtOAc-hexanes gradient). The product slowly crystallized from CH2Cl2-hexanes to afford the title compound as a light yellow solid (0.42 g, 68% yield): MS (ES) m/z 289 (M+1).

Workup

  1. temperatureUpon cooling
  2. concentrationthe mixture was concentrated in vacuo
  3. custompartitioned between EtOAc and H2O
  4. washThe organic phase was washed with sat'd brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash chromatography (0-30% EtOAc-hexanes gradient)
  8. customThe product slowly crystallized from CH2Cl2-hexanes

Sources & evidence

ORD record
ord-da425febc44b48cab506ecc1876c0115
Source dataset
uspto-grants-2011_09
Patent number
US08026262B2

Reaction notes

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