Triethylamine → 4-(2-chloro-5-fluorophenyl)-1-pivaloyl-2-phenyl-2,5-dihydro-1H-pyrrole

HRID 1394919Notes

Reaction equation

HRID 1394919 reaction equation
C(N(CC)CC)C.[C:8](Cl)(=[O:13])[C:9]([CH3:12])([CH3:11])[CH3:10].[Cl: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>[Cl:15][C:16]1[CH:21]=[CH:20][C:19]([F:22])=[CH:18][C:17]=1[C:23]1[CH2:27][N:26]([C:8](=[O:13])[C:9]([CH3:12])([CH3:11])[CH3:10])[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 62493Pivaloyl chlorideHCID 596566114-(2-chloro-5-fluorophenyl)-2-phenyl-2,5-dihydro-1H-pyrrole

Product 1

HCID 586412094-(2-chloro-5-fluorophenyl)-1-pivaloyl-2-phenyl-2,5-dihydro-1H-pyrrole

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triethylamine (149 μL, 1.07 mmol, 10.00 equiv) and pivaloyl chloride (26 μL, 0.214 mmol, 2.00 equiv) were added sequentially to a solution of 4-(2-chloro-5-fluorophenyl)-2-phenyl-2,5-dihydro-1H-pyrrole (1-5, 0.107 mmol, 1 equiv) in dichloromethane (10 mL) at 23° C., and the resulting mixture was stirred for 20 minutes. The reaction mixture was concentrated and the residue purified by reverse-phase LC (H2O/CH3CN gradient w/0.1% TFA present) to provide 4-(2-chloro-5-fluorophenyl)-1-(2,2-dimethylpropanoyl)-2-phenyl-2,5-dihydro-1H-pyrrole (10-1) as a tan solid. 1H NMR (300 MHz, CDCl3) δ 7.39 (dd, 1H, J=8.8, 5.2 Hz), 7.33 (m, 4H), 7.26 (m, 1H), 7.05 (dd, 1H, J=9.2, 3.1 Hz), 6.99 (m, 1H), 6.20 (m, 1H), 5.98 (m, 1H), 5.00 (m, 2H), 1.28 (s, 9H). LRMS m/z (M+H) 358.0 found, 358.1 required.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue purified by reverse-phase LC (H2O/CH3CN gradient w/0.1% TFA present)

Sources & evidence

ORD record
ord-52cf188cbd3840eb8effbd634285b846
Source dataset
uspto-grants-2008_03
Patent number
US07348440B2

Reaction notes

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