N-bromobutanimide → 2-Bromo-3-(4-chlorophenyl)-1h-indol-4-yl methyl sulfide

HRID 857321Notes

Reaction equation

[CH3:1][S:2][C:3]1[C:4]2[C:5]([C:12]3[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=3)=[CH:6][NH:7][C:8]=2[CH:9]=[CH:10][CH:11]=1.C1C(=O)N([Br:26])C(=O)C1>C(Cl)(Cl)(Cl)Cl>[CH3:1][S:2][C:3]1[C:4]2[C:5]([C:12]3[CH:13]=[CH:14][C:15]([Cl:18])=[CH:16][CH:17]=3)=[C:6]([Br:26])[NH:7][C:8]=2[CH:9]=[CH:10][CH:11]=1

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of the indole of Step 6 (650 mg, 2.4 mmol) in CCl4 (15 mL) was added NBS (465 mg, 2.6 mmol). The reaction mixture was heated to 50° C. and stirred for 15 minutes. The resulting suspension was filtered on a SiO2 pad eluted with 50% EtOAc in hexanes and concentrated. The title compound was obtained in a quantitative yield as a brownish solid foam used as such.

Workup

filtrationThe resulting suspension was filtered on a SiO2 pad
washeluted with 50% EtOAc in hexanes
concentrationconcentrated

Sources & evidence

ORD record: ord-d48b109169ef45e988b50bb6d36b0853
Source dataset: uspto-grants-2006_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07144913B2

Reaction notes

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