Cesium carbonate → HCID 59425321, compound

HRID 502284Notes

Reaction equation

HRID 502284 reaction equation
[C:1]([C:3]1[C:11]2[C:6](=[CH:7][C:8]([N+:12]([O-])=O)=[CH:9][CH:10]=2)[NH:5][CH:4]=1)#[N:2].[CH:15]1(Br)[CH2:18][CH2:17][CH2:16]1.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C>[NH2:12][C:8]1[CH:7]=[C:6]2[C:11]([C:3]([C:1]#[N:2])=[CH:4][N:5]2[CH:15]2[CH2:18][CH2:17][CH2:16]2)=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 78110BromocyclobutaneHCID 2831796-Nitro-1H-indole-3-carbonitrile

Product 1

HCID 59425321HCID 59425321, compoundYield 74.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 3-cyano-6-nitroindole (3.74 g, 20.0 mmol), cyclobutylbromide (2.27 mL, 24.0 mmol), Cs2CO3 (13.04 g, 40.0 mmol) in DMF (20 mL) was stirred at 90° C. in a sealed tube for 3 days. After cooling, the mixture was poured into ice-water (200 mL) and the precipitate was filtered, washed with water and transferred to a Paar hydrogenator. The hydrogenation was carried out with 5% Pd/C (1.0 g), in MeOH (50 mL) and EtOAc (50 mL) at 60 psi of H2 for 24 h. The mixture was filtered through Celite, washed with MeOH and concentrated to dryness to provide 6-amino-1-cyclobutyl-3-cyanoindole (3.13 g, 74%).

Workup

  1. temperatureAfter cooling
  2. filtrationthe precipitate was filtered
  3. washwashed with water
  4. waitEtOAc (50 mL) at 60 psi of H2 for 24 h
  5. filtrationThe mixture was filtered through Celite
  6. washwashed with MeOH
  7. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-5aa2f86342d743499e301c61fcb4ccaf
Source dataset
uspto-grants-2010_08
Patent number
US07772271B2

Reaction notes

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