Sodium Carbonate → 3-{3-[2-(2-Ethylimidazol-1-yl)acetyl]phenyl}-5-iso-butyl-N-tert-butylthio-phene-2-sulfonamide

HRID 659699Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 659699
Br[C:2]1[CH:3]=[C:4]([C:8](=[O:17])[CH2:9][N:10]2[CH:14]=[CH:13][N:12]=[C:11]2[CH2:15][CH3:16])[CH:5]=[CH:6][CH:7]=1.[CH2:18]([C:22]1[S:26][C:25]([S:27]([NH:30][C:31]([CH3:34])([CH3:33])[CH3:32])(=[O:29])=[O:28])=[C:24](B(O)O)[CH:23]=1)[CH:19]([CH3:21])[CH3:20].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>[CH2:15]([C:11]1[N:10]([CH2:9][C:8]([C:4]2[CH:3]=[C:2]([C:24]3[CH:23]=[C:22]([CH2:18][CH:19]([CH3:20])[CH3:21])[S:26][C:25]=3[S:27]([NH:30][C:31]([CH3:33])([CH3:32])[CH3:34])(=[O:29])=[O:28])[CH:7]=[CH:6][CH:5]=2)=[O:17])[CH:14]=[CH:13][N:12]=1)[CH3:16]

Komponenten

8

Edukt 3

HCID 10340Sodium CarbonateHCID 11484000(2-(N-(tert-Butyl)sulfamoyl)-5-isobutylthiophen-3-yl)boronic acidHCID 614053531-(3-Bromophenyl)-2-(2-ethylimidazol-1-yl)ethanone

Produkt 1

HCID 671329483-{3-[2-(2-Ethylimidazol-1-yl)acetyl]phenyl}-5-iso-butyl-N-tert-butylthio-phene-2-sulfonamideAusbeute 94 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 702EthanolLösungsmittelHCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a solution of 1-(3-bromophenyl)-2-(2-ethylimidazol-1-yl)ethanone (54.6 mg, 0.186 mmol; see step (a)) in toluene (10 mL) and ethanol (1 mL) was added 5-isobutyl-2-(N-tert-butylaminosulfonyl)thiophene-3-boronic acid (101 mg, 0.317 mmol; see Example 1(c)), Pd(PPh3)4 (12.9 mg, 0.0112 mmol), Na2CO3 (373 μL, 0.745 mmol, 2.0 M aq) and the reaction mixture was stirred for 4 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 purified by flash chromatography using MeOH:CH2Cl2 (5:95) as eluent to give the sub-title compound as a colourless syrup in 94% yield (85.5 mg, 0.175 mmol).

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-beec73cb9e194f069c0d3154decc27c4
Quelldatensatz
uspto-grants-2011_12
Patentnummer
US08080571B2

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