Chlorosuccinimide → N-(2-{[3-chloro-1-(phenylsulfonyl)-1H-indol-5-yl]oxy}ethyl)acetamide

HRID 2423197Notes

Reaction equation

[Cl:1]N1C(=O)CCC1=O.[C:9]1([S:15]([N:18]2[C:26]3[C:21](=[CH:22][C:23]([O:27][CH2:28][CH2:29][NH:30][C:31](=[O:33])[CH3:32])=[CH:24][CH:25]=3)[CH:20]=[CH:19]2)(=[O:17])=[O:16])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>C1COCC1>[Cl:1][C:20]1[C:21]2[C:26](=[CH:25][CH:24]=[C:23]([O:27][CH2:28][CH2:29][NH:30][C:31](=[O:33])[CH3:32])[CH:22]=2)[N:18]([S:15]([C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)(=[O:16])=[O:17])[CH:19]=1

Participants

Conditions

Temperature: 40 °C

Procedure

N-chlorosuccinimide (0.42 g, 3.2 mmol) was added to a solution of N-(2-{[1-(phenylsulfonyl)-1H-indol-5-yl]oxy}ethyl)acetamide (Intermediate 25, 0.95 g, 2.6 mmol) in THF (20 ml) at room temperature. The reaction mixture was stirred at 40° C. for 6 hours. The reaction mixture was evaporated and the crude material was purified by flash chromatography on silica gel using 3% MeOH in DCM as the eluent to give the title compound (1.11 g) as a white solid. MS m/z 393 [M+H]+.

Workup

customThe reaction mixture was evaporated
customthe crude material was purified by flash chromatography on silica gel using 3% MeOH in DCM as the eluent

Sources & evidence

ORD record: ord-ad6316af9b5e45f683b8907eff4eb6b8
Source dataset: uspto-grants-2011_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07960374B2

Reaction notes

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