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

HRID 659702Notes

Reaction equation

HRID 659702 reaction equation
[N:1]1([CH2:10][C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15](Br)[CH:14]=2)=[O:12])[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1.[CH2:20]([C:24]1[S:28][C:27]([S:29]([NH:32][C:33]([CH3:36])([CH3:35])[CH3:34])(=[O:31])=[O:30])=[C:26](B(O)O)[CH:25]=1)[CH:21]([CH3:23])[CH3:22].C([O-])([O-])=O.[Na+].[Na+]>C1(C)C=CC=CC=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:1]1([CH2:10][C:11]([C:13]2[CH:14]=[C:15]([C:26]3[CH:25]=[C:24]([CH2:20][CH:21]([CH3:22])[CH3:23])[S:28][C:27]=3[S:29]([NH:32][C:33]([CH3:35])([CH3:34])[CH3:36])(=[O:31])=[O:30])[CH:16]=[CH:17][CH:18]=2)=[O:12])[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1

Participants

8

Reactant 3

HCID 10340Sodium CarbonateHCID 11484000(2-(N-(tert-Butyl)sulfamoyl)-5-isobutylthiophen-3-yl)boronic acidHCID 432182762-Benzoimidazol-1-yl-1-(3-bromophenyl)ethanone

Product 1

HCID 671328723-[3-(2-Benzoimidazol-1-ylacetyl)phenyl]-5-iso-butyl-N-tert-butylthiophene-2-sulfonamideYield 90%

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 2-benzoimidazol-1-yl-1-(3-bromophenyl)ethanone (42.7 mg, 0.136 mmol; see step (a)) in toluene (7 mL) and ethanol (1 mL) was added 5-isobutyl-2-(N-tert-butylaminosulfonyl)thiophene-3-boronic acid (73.5 mg, 0.230 mmol; see Example 1(c)), Pd(PPh3)4 (9.4 mg, 8.1 μmol) and Na2CO3 (271 μL, 0.542 mmol, 2.0 M aq), and the reaction mixture was stirred for 3 h at 80° 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 MeOH:CH2Cl2 (5:95) as eluent to give the sub-title compound as a colourless syrup in 90% yield (62 mg, 0.122 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-a6ac5473100146a18f1a7a5817120705
Source dataset
uspto-grants-2011_12
Patent number
US08080571B2

Reaction notes

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