Chlorosulfonyl isocyanate → 4-Bromo-1H-indole-3-carbonitrile

HRID 268791Notes

Reaction equation

HRID 268791 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[CH:5][NH:6]2.ClS([N:15]=[C:16]=O)(=O)=O>C(#N)C>[Br:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4]([C:16]#[N:15])=[CH:5][NH:6]2

Participants

4

Reactant 2

HCID 70918Chlorosulfonyl isocyanateHCID 6764944-Bromoindole

Product 1

HCID 27632324-Bromo-1H-indole-3-carbonitrile

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
0 °C

Procedure

To a 0° C. solution of 4-bromoindole (5 g, 25.5 mmol) in acetonitrile (50 ml) was added dropwise chlorsulfonylisocyanate (2.37 ml, 27.3 mmol) over a 5 minute period. The reaction mixture was stirred at 0° C. for 2 hours, and TEA (3.77 ml, 27.0) was added dropwise over a 10 minute period. The reaction mixture was allowed reach room temperature overnight, poured into ice/water mixture (200 ml), and the aqueous layer was extracted with EtOAc. The combined organic extracts were dried over Na2SO4, filtered, concentrated, and purified by flash chromatography to afford 4-bromo-1H-indole-3-carbonitrile LVII as an off-white solid (4.9 g, 87% yield).

Workup

  1. customreach room temperature overnight
  2. extractionthe aqueous layer was extracted with EtOAc
  3. dry with materialThe combined organic extracts were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. custompurified by flash chromatography

Sources & evidence

ORD record
ord-c8f92defc52847b9a968b776b6c9dd92
Source dataset
uspto-grants-2008_11
Patent number
US07446118B2

Reaction notes

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