Pyrrole → HCID 67307858, compound

HRID 2061621Notes

Reaction equation

HRID 2061621 reaction equation
[Li]CCCC.[NH:6]1[CH:10]=[CH:9][CH:8]=[CH:7]1.[F:11][C:12]([F:24])([F:23])[C:13]1[CH:18]=[CH:17][C:16]([S:19](Cl)(=[O:21])=[O:20])=[CH:15][CH:14]=1>C1COCC1.CCOC(C)=O>[F:24][C:12]([F:11])([F:23])[C:13]1[CH:14]=[CH:15][C:16]([S:19]([N:6]2[CH:10]=[CH:9][CH:8]=[CH:7]2)(=[O:21])=[O:20])=[CH:17][CH:18]=1

Participants

6

Reactant 3

HCID 8027PyrroleHCID 27773994-(Trifluoromethyl)benzenesulfonyl chlorideHCID 178418339Butyllithium

Product 1

HCID 67307858HCID 67307858, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

n-BuLi (56 mL, 89.7 mmol) was added to a solution of 1H-pyrrole (6.02 g, 89.7 mmol) in THF (179 mL) at −78° C. over 10 minutes. 4-(trifluoromethyl)benzene-1-sulfonyl chloride (26.3 g, 107.6 mmol) was dissolved in THF (20 mL) and added to the reaction mixture over 30 minutes. The reaction was stirred for 30 minutes then allowed to warm to room temperature and stirred for a further 18 h. The solution was diluted with EtOAc washed with brine and the organic phase was separated, dried (Na2SO4), filtered and concentrated under vacuum and purified on a silica gel column (eluant hexane/EtOAc 99/1 to 4/1, v/v) to give compound 111 (21.4 g, 77.7 mmol, 87%). MS (ESI) 276.1 (M+H).

Workup

  1. additionadded to the reaction mixture over 30 minutes
  2. stirringstirred for a further 18 h
  3. washwashed with brine
  4. customthe organic phase was separated
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum
  8. custompurified on a silica gel column (eluant hexane/EtOAc 99/1 to 4/1

Sources & evidence

ORD record
ord-2ec9ea514b514415981bb37f35ba8b22
Source dataset
uspto-grants-2012_10
Patent number
US08283358B2

Reaction notes

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