N,N'-Dimethylethylenediamine → 2,5-dimethyl-1-(2-trifluoromethyl-phenyl)-1H-pyrrole-3-carboxylic acid (4-dimethylsulfamoyl-3-methyl-phenyl)-amide

HRID 912572Notes

Reaction equation

HRID 912572 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]([CH3:13])[CH3:12])(=[O:10])=[O:9])=[C:4]([CH3:14])[CH:3]=1.[CH3:15][C:16]1[N:17]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[C:31]([F:34])([F:33])[F:32])[C:18]([CH3:24])=[CH:19][C:20]=1[C:21]([NH2:23])=[O:22].C([O-])([O-])=O.[K+].[K+].CNCCNC>CCOC(C)=O.[Cu]I.C1(C)C=CC=CC=1>[CH3:12][N:11]([CH3:13])[S:8]([C:5]1[CH:6]=[CH:7][C:2]([NH:23][C:21]([C:20]2[CH:19]=[C:18]([CH3:24])[N:17]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[C:31]([F:33])([F:32])[F:34])[C:16]=2[CH3:15])=[O:22])=[CH:3][C:4]=1[CH3:14])(=[O:10])=[O:9]

Participants

8

Reactant 4

HCID 8070N,N'-DimethylethylenediamineHCID 11430Potassium CarbonateHCID 595902374-bromo-N,N,2-trimethylbenzenesulfonamideHCID 598082232,5-dimethyl-1-(2-trifluoromethyl-phenyl)-1H-pyrrole-3-carboxamide

Product 1

HCID 598078142,5-dimethyl-1-(2-trifluoromethyl-phenyl)-1H-pyrrole-3-carboxylic acid (4-dimethylsulfamoyl-3-methyl-phenyl)-amideYield 79,246.703%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
120 °C

Procedure

An oven-dried, argon-sparged vial was charged with 4-bromo-2,N,N-trimethyl-benzenesulfonamide (70 mg, 0.25 mmol), 2,5-dimethyl-1-(2-trifluoromethyl-phenyl)-1H-pyrrole-3-carboxamide (85 mg, 0.30 mmol), anhyd K2CO3 (69 mg, 0.50 mmol), and copper (I) iodide (10 mg, 0.05 mmol), and then briefly sparged with argon. To the vial under argon was added anhyd toluene (0.5 mL) and N,N′-dimethyl-ethylenediamine (11 μL, 0.10 mmol), then capped and heated at 120° C. After 24h the reaction mixture was cooled, diluted with EtOAc, filtered through Celite and concentrated under reduced pressure. The crude material was chromatographed (silica, EtOAc/Hex, 0:100 to 50:50) to afford the title compound (95 g, 79%) as a white solid. 1H-NMR (DMSO-d6) δ 9.74 (1H, s), 8.01 (1H, d, J=7.8), 7.92 (1H, app t, J=7.8), 7.78-7.86 (3H, m), 7.71 (1H, d, J=8.3), 7.51 (1H, d, J=7.8), 6.65 (1H, s), 2.69 (6H, s), 2.53 (3H, s), 2.14 (3H, s), 1.88 (3H, s); MS (ESI): 480 (MH+).

Workup

  1. customAn oven-dried, argon-sparged vial
  2. custombriefly sparged with argon
  3. customcapped
  4. filtrationfiltered through Celite
  5. concentrationconcentrated under reduced pressure
  6. customThe crude material was chromatographed (silica, EtOAc/Hex, 0:100 to 50:50)

Sources & evidence

ORD record
ord-add03c3f02e843098325b81e464b4cf5
Source dataset
uspto-grants-2011_09
Patent number
US08026237B2

Reaction notes

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