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1,8-Diazabicyclo(5.4.0)undec-7-ene → N-(4'-bromo-[1,1'-biphenyl]-2-yl)propane-2-sulfonamide

HRID 746763
Notes
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Reaction equation

HRID 746763 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[NH2:14])=[CH:4][CH:3]=1.C1CCN2C(=NCCC2)CC1.[CH:26]([S:29](Cl)(=[O:31])=[O:30])([CH3:28])[CH3:27]>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[NH:14][S:29]([CH:26]([CH3:28])[CH3:27])(=[O:31])=[O:30])=[CH:6][CH:7]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-ene2×HCID 824082-Propanesulfonyl chloride2×HCID 113686332-(4'-Bromophenyl)aniline

Product 1

HCID 57974945N-(4'-bromo-[1,1'-biphenyl]-2-yl)propane-2-sulfonamideYield 75.3%

Reagents, catalysts & solvents 1

HCID 6344Dichloromethane
Solvent

Conditions

Temperature
0 °C

Procedure

Add 4′-bromo-biphenyl-2-ylamine (1.038 g, 4.183 mmol) to CH2Cl2 and cool to 0° C. Add first DBU (2.6 ml, 17.038 mmol), then isopropylsulfonyl chloride (0.95 ml, 8.206 mmol) drop wise to flask and warm flask to room temperature. After 18 hours monitor reaction. If SM is still present, add DBU (1 ml), then isopropylsulfonyl chloride (0.4 ml) and then stir 2 additional hours. Purify resultant product using flash chromatography (Silica gel-25% EtOAc/Hexane) to provide propane-2-sulfonic acid (4′-bromo-biphenyl-2-yl)-amide (1.116 g, 75%). MS(m/e): 351.9(M−1).

Workup

  1. customreaction
  2. customPurify resultant product

Sources & evidence

ORD record
ord-4d3690aded9b44a298c16f635dbc3d8a
Source dataset
uspto-grants-2008_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07393868B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes