n-Butyl lithium → HCID 71254114, compound

HRID 332113Notes

Reaction equation

HRID 332113 reaction equation
[Li+].CCC[CH2-].[F:6][C:7]([F:21])([F:20])[S:8]([NH:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH3:19])[CH:13]=1)(=[O:10])=[O:9].[Br:22][C:23]1[CH:24]=[CH:25][C:26]2[N:27]([CH2:37][CH:38]3[CH2:40][O:39]3)[C:28]3[C:33]([C:34]=2[CH:35]=1)=[CH:32][C:31]([Br:36])=[CH:30][CH:29]=3>O1CCOCC1.C(OCC)(=O)C>[Br:22][C:23]1[CH:24]=[CH:25][C:26]2[N:27]([CH2:37][CH:38]([OH:39])[CH2:40][N:11]([C:12]3[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH3:19])[CH:13]=3)[S:8]([C:7]([F:20])([F:6])[F:21])(=[O:9])=[O:10])[C:28]3[C:33]([C:34]=2[CH:35]=1)=[CH:32][C:31]([Br:36])=[CH:30][CH:29]=3

Participants

6

Reactant 3

HCID 61028n-Butyl lithiumHCID 27754733,6-dibromo-9-((oxiran-2-yl)methyl)-9H-carbazoleHCID 23274414M-MEO CF3-METHANESULFONANILIDE

Product 1

HCID 71254114HCID 71254114, compound

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

N-butyllithium (2.5 M in hexanes, 48 ml) was added dropwise to an ice-cooled solution of 1,1,1-trifluoro-N-(3-methoxyphenyl)methanesulfonamide (22.07 g, 86.5 mmol) in dry dioxane (145 ml) over a 40 minute period. The solution was then stirred at ambient temperature for 15 minutes before addition of 3,6-dibromo-9-(oxiran-2-ylmethyl)-9H-carbazole (25.05 g, 65.7 mmol) followed by heating at 90° C. for an hour. The reaction was cooled then diluted with 1.2 L ethyl acetate and washed several times with water and finally brine. The organic layer was dried over MgSO4, filtered and condensed to give an orange viscous mixture. The residue was dissolved in 150 ml of 60% methylene chloride/hexanes, then concentrated to yellow foam to which a further 150 ml of 60% methylene chloride/hexanes was added and stirred overnight. The mixture was filtered and washed several times with 60% methylene chloride/hexanes until the solid was white giving 20.1 g of 99%

Workup

  1. temperatureThe reaction was cooled
  2. washwashed several times with water and finally brine
  3. dry with materialThe organic layer was dried over MgSO4
  4. filtrationfiltered
  5. customcondensed
  6. customto give an orange viscous mixture
  7. concentrationconcentrated to yellow foam to which a further 150 ml of 60% methylene chloride/hexanes
  8. additionwas added
  9. filtrationThe mixture was filtered
  10. washwashed several times with 60% methylene chloride/hexanes until the solid
  11. customwas white giving 20.1 g of 99%

Sources & evidence

ORD record
ord-d47259d8516f490490846c69441a2388
Source dataset
uspto-grants-2014_11
Patent number
US08877797B2

Reaction notes

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