Chlorosuccinimide → 10-Chloro-2-methyl-8-(phenylsulfonyl)-1,3,4,8-tetrahydro-2H-[1,4]oxazepino[6,7-e]indole

HRID 2423123Notes

Reaction equation

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

Participants

Conditions

Temperature: 50 °C

Procedure

N-chlorosuccinimide (NCS) (29 mg, 0.21 mmol) was added to a solution of 2-methyl-8-(phenylsulfonyl)-1,3,4,8-tetrahydro-2H-[1,4]oxazepino[6,7-e]indole Example 5, 0.050 g, 0.15 mmol) in THF (2 mL) and the reaction mixture was heated at 50° C. overnight. Additional NCS (0.030 g, 0.22 mmol) was added and the mixture was heated for 4 days at 50° C. The mixture was evaporated and the crude material was purified by flash chromatography on silica gel using MeOH:DCM:NEt3 (2:97:1) to give 7.3 mg of a white solid. MS m/z 377 [M+H]+.

Workup

temperaturethe mixture was heated for 4 days at 50° C
customThe mixture was evaporated
customthe crude material was purified by flash chromatography on silica gel

Sources & evidence

ORD record: ord-711972acff84482c9de89d600528ce7b
Source dataset: uspto-grants-2011_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07960374B2

Reaction notes

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