Phosphorus trichloride → 3-(4-Fluoro-phenoxy)-6-methanesulfonyl-2-methyl-1H-indole

HRID 2218233Notes

Reaction equation

HRID 2218233 reaction equation
[CH3:1][S:2]([C:5]1[CH:6]=[C:7]([NH:11]N)[CH:8]=[CH:9][CH:10]=1)(=[O:4])=[O:3].[F:13][C:14]1[CH:24]=[CH:23][C:17]([O:18][CH2:19][C:20](=O)[CH3:21])=[CH:16][CH:15]=1.P(Cl)(Cl)Cl>C1C=CC=CC=1>[F:13][C:14]1[CH:24]=[CH:23][C:17]([O:18][C:19]2[C:8]3[C:7](=[CH:6][C:5]([S:2]([CH3:1])(=[O:4])=[O:3])=[CH:10][CH:9]=3)[NH:11][C:20]=2[CH3:21])=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 24387Phosphorus trichlorideHCID 128146941-(4-Fluorophenoxy)propan-2-oneHCID 22034382(3-Methanesulfonylphenyl)hydrazine

Product 1

HCID 98366983-(4-Fluoro-phenoxy)-6-methanesulfonyl-2-methyl-1H-indoleYield 5.2%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To the solution of (3-methanesulfonyl-phenyl)-hydrazine (1.35 g) and 1-(4-fluoro-phenoxy)-propan-2-one (1.01 g) in benzene at RT was added equimolar amount of PCl3. The reaction mixture was stirred at RT for 1 hour and the solvent was removed in vacuo. The residue was purified by Biotage chromatography, eluted with 10-30% EtOAc/Hexane to yield 0.1 g of 3-(4-fluoro-phenoxy)-6-methanesulfonyl-2-methyl-1H-indole 401 as a light orange powder, MS: 320 ([M+H]+).

Workup

  1. customthe solvent was removed in vacuo
  2. customThe residue was purified by Biotage chromatography
  3. washeluted with 10-30% EtOAc/Hexane

Sources & evidence

ORD record
ord-4346f04b64ea4563a5e84b263045d65c
Source dataset
uspto-grants-2008_08
Patent number
US07410994B2

Reaction notes

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