Toluene → 3-(4-Imidazol-1-ylmethylphenyl)-5-butyl-N-tert-butylthiophene-2-sulfonamide

HRID 1644832Notes

Reaction equation

HRID 1644832 reaction equation
[CH2:1]([C:5]1[S:9][C:8]([S:10]([NH:13][C:14]([CH3:17])([CH3:16])[CH3:15])(=[O:12])=[O:11])=[C:7](B(O)O)[CH:6]=1)[CH2:2][CH2:3][CH3:4].Br[C:22]1[CH:33]=[CH:32][C:25]([CH2:26][N:27]2[CH:31]=[CH:30][N:29]=[CH:28]2)=[CH:24][CH:23]=1.C1(C)C=CC=CC=1.[OH-].[Na+]>CCOC(C)=O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(O)C>[N:27]1([CH2:26][C:25]2[CH:24]=[CH:23][C:22]([C:7]3[CH:6]=[C:5]([CH2:1][CH2:2][CH2:3][CH3:4])[S:9][C:8]=3[S:10]([NH:13][C:14]([CH3:17])([CH3:16])[CH3:15])(=[O:12])=[O:11])=[CH:33][CH:32]=2)[CH:31]=[CH:30][N:29]=[CH:28]1

Participants

8

Reactant 4

HCID 1140TolueneHCID 14798Sodium HydroxideHCID 29895571-(4-Bromobenzyl)-1H-imidazoleHCID 119939115-Butyl-2-(N-tert-butylaminosulfonyl)thiophene-3-boronic acid

Product 1

HCID 119940313-(4-Imidazol-1-ylmethylphenyl)-5-butyl-N-tert-butylthiophene-2-sulfonamide

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

5-Butyl-2-(N-tert-butylaminosulfonyl)thiophene-3-boronic acid (300 mg, 1.27 mmol, see step (b) above), 1-(4-bromobenzyl)-1H-imidazole (606 mg, 1.90 mmol, see Example 1(d) above), toluene (15 mL), ethanol (4 mL), NaOH (1.0 M, 4.0 mL, 5.1 mmol) and Pd(PPh3)4 (43.9 mg, 0.038 mmol) were mixed under N2. The mixture was warmed to reflux for 2 hours, diluted with EtOAc (50 mL), washed with water and brine, and dried over MgSO4. The solvent was removed and the residue was separated by column chromatography using chloroform:methanol (20:1) as eluent. The product was not completely pure but was used in the next step without further purification.

Workup

  1. temperatureThe mixture was warmed
  2. temperatureto reflux for 2 hours
  3. washwashed with water and brine
  4. dry with materialdried over MgSO4
  5. customThe solvent was removed
  6. customthe residue was separated by column chromatography
  7. customwas used in the next step without further purification

Sources & evidence

ORD record
ord-6a03ac07dd2d4ff79f02eef9d7a4d739
Source dataset
uspto-grants-2012_02
Patent number
US08124638B2

Reaction notes

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