Chlorosuccinimide → HCID 66765354, compound

HRID 1466912Notes

Reaction equation

ClN1C(=O)CCC1=O.[Br:9][C:10]1[CH:11]=[C:12]([SH:16])[CH:13]=[CH:14][CH:15]=1.[CH2:17]([O:19][C:20]([C:22]1[NH:23][C:24]2[C:29]([CH:30]=1)=[CH:28][CH:27]=[C:26]([Cl:31])[CH:25]=2)=[O:21])[CH3:18]>C(Cl)Cl>[CH2:17]([O:19][C:20]([C:22]1[NH:23][C:24]2[C:29]([C:30]=1[S:16][C:12]1[CH:13]=[CH:14][CH:15]=[C:10]([Br:9])[CH:11]=1)=[CH:28][CH:27]=[C:26]([Cl:31])[CH:25]=2)=[O:21])[CH3:18]

Participants

Conditions

Temperature: -78 °C

Procedure

N-Chlorosuccinimide (1.59 g, 12 mmol) was dissolved in DCM (100 mL) and the solution was cooled to −78° C. 3-Bromothiophenol (1.24 mL, 12 mmol) was added dropwise and the reaction stirred for 30 minutes. Then, 6-chloro-1H-indole-2-carboxylic acid ethyl ester (2.2 g, 10 mmol) as a solution in DCM was added in 3 portions and the reaction was allowed to slowly warm to room temperature and continued stirring overnight. The reaction mixture was concentrated then purified by silica gel chromatography (0-30% EtOAc in hexanes) to afford the title compound.

Workup

temperatureto slowly warm to room temperature
stirringcontinued stirring overnight
concentrationThe reaction mixture was concentrated
customthen purified by silica gel chromatography (0-30% EtOAc in hexanes)

Sources & evidence

ORD record: ord-eaa68f30dae14073bdf610c81988b562
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09000025B2

Reaction notes

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