Toluene → 3-[3-(2-Benzoimidazol-1-ylacetyl)phenyl]-5-iso-butyl-N-tert-butylthiophene-2-sulfonamide

HRID 659704Notes

Reaction equation

HRID 659704 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH2:8][CH2:9][N:10]2[CH:14]=[CH:13][N:12]=[CH:11]2)[CH:5]=[CH:6][CH:7]=1.[CH2:15]([C:19]1[S:23][C:22]([S:24]([NH:27][C:28]([CH3:31])([CH3:30])[CH3:29])(=[O:26])=[O:25])=[C:21](B(O)O)[CH:20]=1)[CH:16]([CH3:18])[CH3:17].C([O-])([O-])=[O:36].[Na+].[Na+].[C:41]1(C)C=C[CH:44]=[CH:43][CH:42]=1>C(O)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>[N:10]1([CH2:9][C:8]([C:4]2[CH:3]=[C:2]([C:21]3[CH:20]=[C:19]([CH2:15][CH:16]([CH3:18])[CH3:17])[S:23][C:22]=3[S:24]([NH:27][C:28]([CH3:31])([CH3:30])[CH3:29])(=[O:26])=[O:25])[CH:7]=[CH:6][CH:5]=2)=[O:36])[C:14]2[CH:41]=[CH:42][CH:43]=[CH:44][C:13]=2[N:12]=[CH:11]1

Participants

8

Reactant 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 11484000(2-(N-(tert-Butyl)sulfamoyl)-5-isobutylthiophen-3-yl)boronic acidHCID 671331731-[2-(3-Bromophenyl)ethyl]-1H-imidazole

Product 1

HCID 671328723-[3-(2-Benzoimidazol-1-ylacetyl)phenyl]-5-iso-butyl-N-tert-butylthiophene-2-sulfonamideYield 91%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 1-[2-(3-bromophenyl)ethyl]-1H-imidazole (51.5 mg, 0.205 mmol; see step (a)) in toluene (10 mL) and ethanol (1 mL) was added 5-isobutyl-2-(N-tert-butylaminosulfonyl)thiophene-3-boronic acid (111.3 mg, 0.349 mmol; see Example 1(c)), Pd(PPh3)4 (14.2 mg, 23.4 μmol) and Na2CO3 (410 μL, 0.820 mmol, 2.0 M aq), and the reaction mixture was stirred for 4 h at 90° C. The reaction mixture was diluted with water (10 mL) and extracted with EtOAc. The combined organic phase was dried (over anhydrous MgSO4), concentrated in vacuo, and the residue was purified by flash chromatography using EtOAc:hexane (3:7) as eluent to give the sub-title compound in 91% yield (83.3 mg, 0.187 mmol).

Workup

  1. extractionextracted with EtOAc
  2. dry with materialThe combined organic phase was dried (over anhydrous MgSO4)
  3. concentrationconcentrated in vacuo
  4. customthe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-6d62863b004e4dfb8dc7ff3c96b74123
Source dataset
uspto-grants-2011_12
Patent number
US08080571B2

Reaction notes

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