N-bromobutanimide → HCID 11989685, compound

HRID 2220286Notes

Reaction equation

HRID 2220286 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[S:7][C:8]2[CH:14]=[CH:13][C:12]([NH:15][S:16]([C:19]3[CH:24]=[CH:23][C:22]([C:25]([CH3:28])([CH3:27])[CH3:26])=[CH:21][CH:20]=3)(=[O:18])=[O:17])=[CH:11][C:9]=2[CH:10]=1)=[O:5])[CH3:2].[Br:29]N1C(=O)CCC1=O>>[CH2:1]([O:3][C:4]([C:6]1[S:7][C:8]2[CH:14]=[CH:13][C:12]([NH:15][S:16]([C:19]3[CH:20]=[CH:21][C:22]([C:25]([CH3:27])([CH3:26])[CH3:28])=[CH:23][CH:24]=3)(=[O:17])=[O:18])=[CH:11][C:9]=2[C:10]=1[Br:29])=[O:5])[CH3:2]

Participants

3

Reactant 2

HCID 67184N-bromobutanimideHCID 11989684HCID 11989684, compound

Product 1

HCID 11989685HCID 11989685, compoundYield 94%

Procedure

According to Step 4, after reaction of 5-(4-tert-Butylbenzenesulfonylamino)-1-benzothiophene-2-carboxylic acid ethyl ester (5.34 mg, 12.79 mmol) from Example 1b) with N-bromosuccinimide (2.30 g, 12.7 mmol) followed by chromatographic purification (silica gel, hexane/ethyl acetate (0-70% ethyl acetate)), the desired compound is obtained at 94% yield (5.98 g).

Workup

  1. customfollowed by chromatographic purification (silica gel, hexane/ethyl acetate (0-70% ethyl acetate))

Sources & evidence

ORD record
ord-7ca6af5bc98b46e192f41d05b58d5a8b
Source dataset
uspto-grants-2008_08
Patent number
US07417066B2

Reaction notes

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