Cesium carbonate → 1-cyclobutyl-6-methoxy-1H-indole-3-carbonitrile

HRID 1027989Notes

Reaction equation

HRID 1027989 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([C:7]([C:12]#[N:13])=[CH:8][NH:9]2)=[CH:5][CH:4]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[CH:20]1(Br)[CH2:23][CH2:22][CH2:21]1>CN(C=O)C>[CH:20]1([N:9]2[C:10]3[C:6](=[CH:5][CH:4]=[C:3]([O:2][CH3:1])[CH:11]=3)[C:7]([C:12]#[N:13])=[CH:8]2)[CH2:23][CH2:22][CH2:21]1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 78110BromocyclobutaneHCID 534011976-Methoxy-1H-indole-3-carbonitrile

Product 1

HCID 594261981-cyclobutyl-6-methoxy-1H-indole-3-carbonitrileYield 96.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

To 6-methoxy-1H-indole-3-carbonitrile (98.2 g, 0.57 mol) was added cesium carbonate (430 g, 1.32 mol), DMF (165 mL) and cyclobutylbromide (96%, 67.5 mL, 0.69 mol). The mixture was heated to 90° C. and stirred overnight. The mixture was cooled to 37° C. and poured into ice water (500 mL), washing in with water. After stirring for 1 hour the precipitate was collected on a filter and dried under a stream of nitrogen to give 1-cyclobutyl-6-methoxy-1H-indole-3-carbonitrile as a tan solid (124.1 g, 96%).

Workup

  1. temperatureThe mixture was cooled to 37° C.
  2. washwashing in with water
  3. stirringAfter stirring for 1 hour the precipitate
  4. customwas collected on
  5. filtrationa filter
  6. customdried under a stream of nitrogen

Sources & evidence

ORD record
ord-f22f3f9949c643fabdfd4262d1eacb56
Source dataset
uspto-grants-2014_05
Patent number
US08735414B2

Reaction notes

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