Chlorosuccinimide → HCID 66765139, compound

HRID 1466916Notes

Reaction equation

HRID 1466916 reaction equation
ClN1C(=O)CCC1=O.[Br:9][C:10]1[CH:11]=[C:12]([SH:16])[CH:13]=[CH:14][CH:15]=1.[Cl:17][C:18]1[CH:26]=[C:25]2[C:21]([CH:22]=[CH:23][NH:24]2)=[CH:20][CH:19]=1>C(Cl)Cl>[Br:9][C:10]1[CH:11]=[C:12]([S:16][C:22]2[C:21]3[C:25](=[CH:26][C:18]([Cl:17])=[CH:19][CH:20]=3)[NH:24][CH:23]=2)[CH:13]=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 31398ChlorosuccinimideHCID 80597m-BromobenzenethiolHCID 871116-Chloroindole

Product 1

HCID 66765139HCID 66765139, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-78 °C

Procedure

N-chlorosuccinimide (1.93 g, 14.5 mmol) was dissolved in DCM (120 mL) and cooled to −78° C. 3-Bromothiophenol was added and the reaction was warmed to 0° C. After 1 hour, a solution of 6-chloroindole (2.0 g, 13.2 mmol) in DCM (20 mL) was added via canula. The reaction was stirred at 0° C. for 3 hours after which time it was submitted to aqueous workup and purification by silica gel chromatography (0-50% EtOAc in hexanes) to give the title compound.

Workup

  1. temperaturethe reaction was warmed to 0° C
  2. customwas submitted to aqueous workup and purification by silica gel chromatography (0-50% EtOAc in hexanes)

Sources & evidence

ORD record
ord-a1a9edafb6af4ad9afa523d97b31cc48
Source dataset
uspto-grants-2015_04
Patent number
US09000025B2

Reaction notes

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