Ethanol → 3-[3-(2-Thiophen-3-yl-imidazol-1-ylmethyl)-phenyl]-5-iso-butyl-N-tert-butyl-thiophene-2-sulfonamide

HRID 659691Notes

Reaction equation

HRID 659691 reaction equation
Br[C:2]1[N:3]([CH2:7][C:8]2[CH:9]=[C:10]([C:14]3[CH:18]=[C:17]([CH2:19][CH:20]([CH3:22])[CH3:21])[S:16][C:15]=3[S:23]([NH:26][C:27]([CH3:30])([CH3:29])[CH3:28])(=[O:25])=[O:24])[CH:11]=[CH:12][CH:13]=2)[CH:4]=[CH:5][N:6]=1.C(O)C.[S:34]1[CH:38]=[CH:37][C:36](B(O)O)=[CH:35]1.[OH-].[Na+]>C1(C)C=CC=CC=1.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>[S:34]1[CH:38]=[CH:37][C:36]([C:2]2[N:3]([CH2:7][C:8]3[CH:9]=[C:10]([C:14]4[CH:18]=[C:17]([CH2:19][CH:20]([CH3:22])[CH3:21])[S:16][C:15]=4[S:23]([NH:26][C:27]([CH3:30])([CH3:29])[CH3:28])(=[O:25])=[O:24])[CH:11]=[CH:12][CH:13]=3)[CH:4]=[CH:5][N:6]=2)=[CH:35]1

Participants

8

Reactant 4

HCID 702EthanolHCID 14798Sodium HydroxideHCID 581760Thiophene-3-boronic acid2×HCID 671329713-[3-(2-bromoimidazol-1-ylmethyl)phenyl]-5-iso-butyl-N-tert-butylthiophene-2-sulfonamide

Product 1

HCID 671331003-[3-(2-Thiophen-3-yl-imidazol-1-ylmethyl)-phenyl]-5-iso-butyl-N-tert-butyl-thiophene-2-sulfonamideYield 71%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalyst2×HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 3-[3-(2-bromoimidazol-1-ylmethyl)phenyl]-5-iso-butyl-N-tert-butylthiophene-2-sulfonamide (61.7 mg, 0.121 mmol; see Example 11((b)) in toluene (5 mL) and ethanol (0.5 mL) was added 3-thienyl boronic acid (77.3 mg, 0.604 mmol), Pd(PPh3)4 (8.4 mg, 7.25 μmol) and NaOH (0.48 mL, 0.725 mmol, 1.5 M aq), and the reaction mixture stirred for 4 h at 90° C. Another portion of 3-thienyl boronic acid (60.0 mg, 0.469 mmol) and Pd(PPh3)4 (5.0 mg, 4.3 μmol) was added and the reaction was stirred overnight at 90° C. The reaction mixture was diluted with EtOAc (30 mL) and washed with water, dried (over anhydrous MgSO4), concentrated in vacuo, and the residue purified by flash chromatography using EtOAc:hexane (8:2 to 9:1) as eluent to give the sub-title compound in 71% yield (44.3 mg, 0.0862 mmol).

Workup

  1. stirringthe reaction was stirred overnight at 90° C
  2. washwashed with water
  3. dry with materialdried (over anhydrous MgSO4)
  4. concentrationconcentrated in vacuo
  5. customthe residue purified by flash chromatography

Sources & evidence

ORD record
ord-fcc4a3d835e549e7aa271a45f2fe3da8
Source dataset
uspto-grants-2011_12
Patent number
US08080571B2

Reaction notes

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