Bromocyclobutane → 1-cyclobutyl-6-ethylsulfanyl-1H-indole-3-carbonitrile

HRID 502291Notes

Reaction equation

HRID 502291 reaction equation
[CH2:1]([S:3][C:4]1[CH:12]=[C:11]2[C:7]([C:8]([C:13]#[N:14])=[CH:9][NH:10]2)=[CH:6][CH:5]=1)[CH3:2].[CH:15]1(Br)[CH2:18][CH2:17][CH2:16]1>CN(C=O)C>[CH:15]1([N:10]2[C:11]3[C:7](=[CH:6][CH:5]=[C:4]([S:3][CH2:1][CH3:2])[CH:12]=3)[C:8]([C:13]#[N:14])=[CH:9]2)[CH2:18][CH2:17][CH2:16]1

Participants

4

Reactant 2

HCID 78110BromocyclobutaneHCID 594261306-ethylsulfanyl-1H-indole-3-carbonitrile

Product 1

HCID 594261191-cyclobutyl-6-ethylsulfanyl-1H-indole-3-carbonitrileYield 96%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
85 °C

Procedure

A mixture of 6-ethylsulfanyl-1H-indole-3-carbonitrile (2.13 g, 10.5 mmol) Cs2CO3 (6.9 g, 21 mmol), cyclobutyl bromide (1.78 g, 13.2 mmol) and DMF (20 mL) was heated to 85° C. overnight and, after cooling, partitioned between ethyl acetate and water. The organic layer was washed with water, brine, dried over Mg2SO4, concentrated and purified on silica gel (EtOAc/hexane 5% to 30%) to provide 1-cyclobutyl-6-ethylsulfanyl-1H-indole-3-carbonitrile (2.58 g, 96%) as a light-yellow oil.

Workup

  1. temperatureafter cooling
  2. custompartitioned between ethyl acetate and water
  3. washThe organic layer was washed with water, brine
  4. dry with materialdried over Mg2SO4
  5. concentrationconcentrated
  6. custompurified on silica gel (EtOAc/hexane 5% to 30%)

Sources & evidence

ORD record
ord-d753f2b1e31641ae8fbe360fe0460f5c
Source dataset
uspto-grants-2010_08
Patent number
US07772271B2

Reaction notes

Loading…