Cesium carbonate → N-(5-bromo-pyridin-3-ylmethyl)-2-chloro-N-isobutyl-benzenesulfonamide

HRID 1665065Notes

Reaction equation

HRID 1665065 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([NH:11][CH2:12][CH:13]([CH3:15])[CH3:14])(=[O:10])=[O:9].Cl.[Br:17][C:18]1[CH:19]=[N:20][CH:21]=[C:22]([CH2:24]Cl)[CH:23]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C(=O)C>[Br:17][C:18]1[CH:23]=[C:22]([CH2:24][N:11]([CH2:12][CH:13]([CH3:15])[CH3:14])[S:8]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[Cl:1])(=[O:9])=[O:10])[CH:21]=[N:20][CH:19]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 84693762-chloro-N-isobutyl-benzenesulfonamideHCID 125150693-Bromo-5-(chloromethyl)pyridine hydrochloride

Product 1

HCID 67440142N-(5-bromo-pyridin-3-ylmethyl)-2-chloro-N-isobutyl-benzenesulfonamide

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

In analogy to example 10, step 3, 2-chloro-N-isobutyl-benzenesulfonamide (example 42, step 1) was reacted with 3-bromo-5-(chloromethyl)pyridine hydrochloride and cesium carbonate in N,N-dimethylacetamide to give N-(5-bromo-pyridin-3-ylmethyl)-2-chloro-N-isobutyl-benzenesulfonamide as a colorless oil. MS: 417.2 ([M+H]+)

Sources & evidence

ORD record
ord-a6545a0e15c24c7680ab0b948b331cdc
Source dataset
uspto-grants-2011_10
Patent number
US08039493B2

Reaction notes

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