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

HRID 659693Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 659693
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.[S:31]1[CH:35]=[CH:34][CH:33]=[C:32]1B(O)O.[OH-].[Na+]>C1(C)C=CC=CC=1.C(O)C.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:31]1[CH:35]=[CH:34][CH:33]=[C:32]1[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

Komponenten

8

Edukt 3

HCID 14798Sodium HydroxideHCID 27339602-Thiopheneboronic acid2×HCID 671329713-[3-(2-bromoimidazol-1-ylmethyl)phenyl]-5-iso-butyl-N-tert-butylthiophene-2-sulfonamide

Produkt 1

HCID 671328453-[3-(2-Thiophen-2-yl-imidazol-1-ylmethyl)phenyl]-5-iso-butyl-N-tert-butyl-thiophene-2-sulfonamideAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 178418397HCID 178418397, VerbindungKatalysator2×HCID 702EthanolLösungsmittelHCID 1140TolueneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

To a solution of 3-[3-(2-bromoimidazol-1-ylmethyl)phenyl]-5-iso-butyl-N-tert-butylthiophene-2-sulfonamide (22 mg, 0.0431 mmol; see example 11 (b)) in toluene (5 mL) and ethanol (0.5 mL) was added 2-thienyl boronic acid (27.6 mg, 0.216 mmol), Pd(PPh3)4 (3.0 mg, 2.59 μmol) and NaOH (0.17 mL, 0.26 mmol, 1.5 M aq), and the reaction mixture stirred for 4 h at 90° C. Another portion of 2-thienyl boronic acid (27.6 mg, 0.216 mmol) and Pd(PPh3)4 (3.0 mg, 2.6 mmol) 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 (7:3) as eluent to give the sub-title compound in 90% yield (20 mg, 0.039 mmol).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-969c01e0ad364e1e9ea5d772f743952e
Quelldatensatz
uspto-grants-2011_12
Patentnummer
US08080571B2

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