Indole → N-Boc 1H-indole-3-sulfonamide

HRID 1947052Notes

Reaction equation

HRID 1947052 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[C:10]([NH:17][S:18](Cl)(=[O:20])=[O:19])([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11].O>C1COCC1>[C:10]([NH:17][S:18]([C:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[NH:1][CH:2]=1)(=[O:19])=[O:20])([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11]

Participants

5

Reactant 3

HCID 798IndoleHCID 962WaterHCID 15677406tert-butyl N-(chlorosulfonyl)carbamate

Product 1

HCID 86620846N-Boc 1H-indole-3-sulfonamideYield 53%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

TEA (4.2 mL, 30 mmol) was added to a solution of indole (1.17 g, 10 mmol) in dry THF (12.0 mL) at 0° C. and stirred for 10 min. N-Boc sulfamoyl chloride (4.31 g, 20 mmol) was added, the mixture allowed to warm to RT, and stirred overnight. The reaction mixture was poured into water, and the crude product extracted into EtOAc. The organic layer was evaporated to dryness, and dried under vacuum overnight to provide N-Boc 1H-indole-3-sulfonamide (1.57 g, 53% yield).

Workup

  1. stirringstirred overnight
  2. extractionthe crude product extracted into EtOAc
  3. customThe organic layer was evaporated to dryness
  4. customdried under vacuum overnight

Sources & evidence

ORD record
ord-7298455f24e64ff289f99bf814e89cdd
Source dataset
uspto-grants-2013_03
Patent number
US08399462B2

Reaction notes

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