Pyridine → n-(1h-Indol-7-yl)methanesulfonamide

HRID 13693

Reaction equation

HRID 13693 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2[NH2:10])[CH:3]=[CH:2]1.N1C=CC=CC=1.[CH3:17][S:18](Cl)(=[O:20])=[O:19]>ClCCl>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2[NH:10][S:18]([CH3:17])(=[O:20])=[O:19])[CH:3]=[CH:2]1

Participants

5

Reactant 3

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 1116347-Aminoindole

Product 1

HCID 20231824n-(1h-Indol-7-yl)methanesulfonamideYield 94%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Stir 1H-indol-7-ylamine with pyridine (1 equivalent) and methanesulfonyl chloride (1 equivalent) in dichloromethane for 12 hrs. Wash the reaction with 1N hydrochloric acid and water, dry over magnesium sulfate, and evaporate. Recrystallize the residue from isopropanol to obtain the title product as a purple solid (94%). MS (ES+), 210 (M), MS (ES−), 209 (M−1). LC/MS shows 95% purity.

Workup

  1. washWash
  2. customthe reaction with 1N hydrochloric acid and water
  3. dry with materialdry over magnesium sulfate
  4. customevaporate
  5. customRecrystallize the residue from isopropanol

Sources & evidence

ORD record
ord-54e3deaf4b5a4dd0936ca7f5174fa939
Source dataset
uspto-grants-2010_06
Patent number
US07728150B2

Linked notes

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