Benzenesulfonyl chloride → HCID 58356346, compound

HRID 244704Notes

Reaction equation

HRID 244704 reaction equation
[Br:1][C:2]1[CH:10]=[C:9]([NH2:11])[CH:8]=[C:7]2[C:3]=1[CH:4]=[CH:5][NH:6]2.C(N(CC)CC)C.[C:19]1([S:25](Cl)(=[O:27])=[O:26])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>N1C=CC=CC=1>[Br:1][C:2]1[CH:10]=[C:9]([NH:11][S:25]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)(=[O:27])=[O:26])[CH:8]=[C:7]2[C:3]=1[CH:4]=[CH:5][NH:6]2

Participants

5

Reactant 3

HCID 7369Benzenesulfonyl chlorideHCID 8471TriethylamineHCID 247279974-Bromo-1H-indol-6-amine

Product 1

HCID 58356346HCID 58356346, compoundYield 54.5%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

4-Bromo-6-amino indole (100 mg, 0.47 mmol) and triethylamine (0.1 ml, 0.71 mmol) were stirred together in pyridine at 0° C. Benzene sulphonyl chloride (84 mg, 0.47 mmol) was then added and the mixture stirred for 1 hour, then allowed to warm to room temperature. The mixture was loaded directly onto an aminopropyl cartridge (10 g) and eluted with methanol. Solvent was evaporated to afford the title compound as an orange/brown gum (90 mg).

Workup

  1. washeluted with methanol
  2. customSolvent was evaporated

Sources & evidence

ORD record
ord-3b623feab5b14f4eb718041c843f42e4
Source dataset
uspto-grants-2014_02
Patent number
US08658635B2

Reaction notes

Loading…