Pyridine → N-(3-pyridyl)indole 3-propyl benzenesulfonate

HRID 485344Notes

Reaction equation

HRID 485344 reaction equation
[OH:1]CCC[C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[N:7]([C:14]2[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=2)[CH:6]=1.[C:20]1([S:26](Cl)(=[O:28])=[O:27])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.N1C=C[CH:33]=[CH:32][CH:31]=1>>[N:16]1[CH:17]=[CH:18][CH:19]=[C:14]([N:7]2[C:8]3[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=3)[CH:5]=[CH:6]2)[CH:15]=1.[C:20]1([S:26]([O:28][CH2:31][CH2:32][CH3:33])(=[O:1])=[O:27])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

4

Reactant 3

HCID 1049PyridineHCID 7369Benzenesulfonyl chlorideHCID 202702043-(3-hydroxypropyl)-N-(3-pyridyl)indole

Product 1

HCID 86740258N-(3-pyridyl)indole 3-propyl benzenesulfonate

Procedure

A solution of 1.0 g of 3-(3-hydroxypropyl)-N-(3-pyridyl)indole in 40 ml of dry pyridine at 0° is treated with 0.7 g of benzenesulfonyl chloride and stored at 0° for 14 hours. The solvent is evaporated and the residue is partitioned between ethyl ether and aqueous sodium bicarbonate solution. The organic phase is separated, dried over potassium carbonate and evaporated to yield crude N-(3-pyridyl)indole-3-propyl benzenesulfonate as an oil which is used without further purification.

Workup

  1. customThe solvent is evaporated
  2. customthe residue is partitioned between ethyl ether and aqueous sodium bicarbonate solution
  3. customThe organic phase is separated
  4. dry with materialdried over potassium carbonate
  5. customevaporated

Sources & evidence

ORD record
ord-6228a7a63c294f7cb98f42afe67a3683
Source dataset
uspto-grants-1985_08
Patent number
US04536505

Reaction notes

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