Triethylamine → HCID 58356413, compound

HRID 244703Notes

Reaction equation

HRID 244703 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.[S:19](Cl)([CH3:22])(=[O:21])=[O:20]>N1C=CC=CC=1>[Br:1][C:2]1[CH:10]=[C:9]([NH:11][S:19]([CH3:22])(=[O:21])=[O:20])[CH:8]=[C:7]2[C:3]=1[CH:4]=[CH:5][NH:6]2

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 247279974-Bromo-1H-indol-6-amine

Product 1

HCID 58356413HCID 58356413, compoundYield 80.9%

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. Mesyl chloride (54 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 and the residue was further purified by chromatography on silica (20 g cartridge) eluting with 0-25% methanol in DCM over 20 mins to afford the title compound as a orange/brown gum (110 mg).

Workup

  1. washeluted with methanol
  2. customSolvent was evaporated
  3. customthe residue was further purified by chromatography on silica (20 g cartridge)
  4. washeluting with 0-25% methanol in DCM over 20 mins

Sources & evidence

ORD record
ord-550ff481ec7d44d286621b435f11a16b
Source dataset
uspto-grants-2014_02
Patent number
US08658635B2

Reaction notes

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