Triethylamine → 4-(2,5-difluorophenyl)-2-phenyl-1-(vinylsulfonyl)-2,5-dihydro-1H-pyrrole

HRID 1394918Notes

Reaction equation

HRID 1394918 reaction equation
C(N(CC)CC)C.Cl[CH2:9][CH2:10][S:11](Cl)(=[O:13])=[O:12].[F:15][C:16]1[CH:21]=[CH:20][C:19]([F:22])=[CH:18][C:17]=1[C:23]1[CH2:27][NH:26][CH:25]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH:24]=1>ClCCl>[F:15][C:16]1[CH:21]=[CH:20][C:19]([F:22])=[CH:18][C:17]=1[C:23]1[CH2:27][N:26]([S:11]([CH:10]=[CH2:9])(=[O:13])=[O:12])[CH:25]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH:24]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 15385Ethanesulfonylchloride, 2-chloro-HCID 590017764-(2,5-difluorophenyl)-2-phenyl-2,5-dihydro-1H-pyrrole

Product 1

HCID 586412054-(2,5-difluorophenyl)-2-phenyl-1-(vinylsulfonyl)-2,5-dihydro-1H-pyrrole

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triethylamine (122 μL, 0.874 mmol, 5.00 equiv) and 2-chloroethanesulfonyl chloride (29 mg, 0.175 mmol, 1.00 equiv) were added sequentially to a solution of 4-(2,5-difluorophenyl)-2-phenyl-2,5-dihydro-1H-pyrrole (2-4, 45 mg, 0.175 mmol, 1 equiv) in dichloromethane (10 mL) at 23° C., and the resulting mixture was stirred for 1 hour. The reaction mixture was partitioned between saturated aqueous sodium bicarbonate solution (50 mL) and ethyl acetate (2×50 mL). The combined organic layers were dried over sodium sulfate and were concentrated to provide 4-(2,5-difluorophenyl)-2-phenyl-1-(vinylsulfonyl)-2,5-dihydro-1H-pyrrole (8-1) as a brown oil. LRMS m/z (M+H) 348.0 found, 348.1 required.

Workup

  1. customThe reaction mixture was partitioned between saturated aqueous sodium bicarbonate solution (50 mL) and ethyl acetate (2×50 mL)
  2. dry with materialThe combined organic layers were dried over sodium sulfate
  3. concentrationwere concentrated

Sources & evidence

ORD record
ord-a9f4c6b0fcff49e0b6d72e10d36d2e1f
Source dataset
uspto-grants-2008_03
Patent number
US07348440B2

Reaction notes

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