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

HRID 1716663Notes

Reaction equation

HRID 1716663 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-f71d0473fa5b42a8b07b70b4a9f07b2d
Source dataset
uspto-grants-2010_09
Patent number
US07803830B2

Reaction notes

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