Ethyl Acetate → N-(3-(3,6-dibromo-9H-carbazol-9-yl)-2-hydroxypropyl)-N-(3-methoxyphenyl)-4-nitrobenzenesulfonamide

HRID 404270Notes

Reaction equation

HRID 404270 reaction equation
CO[C:3]1[CH:8]=[CH:7][C:6]([NH:9][S:10]([C:13]2[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][CH:14]=2)(=[O:12])=[O:11])=[CH:5][CH:4]=1.C([Li])CCC.[Br:27][C:28]1[CH:29]=[CH:30][C:31]2[N:32]([CH2:42][CH:43]3[CH2:45][O:44]3)[C:33]3[C:38]([C:39]=2[CH:40]=1)=[CH:37][C:36]([Br:41])=[CH:35][CH:34]=3.C[CH2:47][O:48]C(C)=O>C1(C)C=CC=CC=1>[Br:27][C:28]1[CH:29]=[CH:30][C:31]2[N:32]([CH2:42][CH:43]([OH:44])[CH2:45][N:9]([C:6]3[CH:5]=[CH:4][CH:3]=[C:8]([O:48][CH3:47])[CH:7]=3)[S:10]([C:13]3[CH:14]=[CH:15][C:16]([N+:19]([O-:21])=[O:20])=[CH:17][CH:18]=3)(=[O:11])=[O:12])[C:33]3[C:38]([C:39]=2[CH:40]=1)=[CH:37][C:36]([Br:41])=[CH:35][CH:34]=3

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 750280N-(4-methoxyphenyl)-4-nitrobenzenesulfonamideHCID 27754733,6-dibromo-9-((oxiran-2-yl)methyl)-9H-carbazoleHCID 178418339Butyllithium

Product 1

HCID 58065820N-(3-(3,6-dibromo-9H-carbazol-9-yl)-2-hydroxypropyl)-N-(3-methoxyphenyl)-4-nitrobenzenesulfonamideYield 88%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A heterogeneous mixture of N-(4-methoxyphenyl)-4-nitrobenzenesulfonamide (100.2 mg, 0.32 mmol) in toluene (2.5 ml, 0.13 M) under a N2 atmosphere was cooled in a dry ice/acetone bath before dropwise addition of n-butyllithium (200 ul of 1.78 M in hexanes, 0.36 mmol). The reaction was stirred at −78° C. for 10 minutes before addition of carbazole epoxide 2-A. The heterogeneous mixture was stirred at room temperature for 5 minutes before heating at 100° C. for 48 hours. The cooled reaction was diluted with EtOAc and washed three times with 5% acetic acid solution, followed by a brine wash. The organic layer was dried over Na2SO4, filtered and condensed. The crude mixture was purified in 100% dichloromethane. Yield=88%

Workup

  1. temperaturebefore heating at 100° C. for 48 hours
  2. customThe cooled reaction
  3. washwashed three times with 5% acetic acid solution
  4. washwash
  5. dry with materialThe organic layer was dried over Na2SO4
  6. filtrationfiltered
  7. customcondensed
  8. customThe crude mixture was purified in 100% dichloromethane

Sources & evidence

ORD record
ord-b8504f09ca8743ed84eb24ff4bbb4939
Source dataset
uspto-grants-2014_06
Patent number
US08748473B2

Reaction notes

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