Cesium carbonate → N-(4-(4-methyl-1H-imidazol-1-yl)benzyl)biphenyl-4-carboxamide

HRID 711281

Reaktionsgleichung

Reaktionsgleichung von HRID 711281
Br[C:2]1[CH:23]=[CH:22][C:5]([CH2:6][NH:7][C:8]([C:10]2[CH:15]=[CH:14][C:13]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[CH:12][CH:11]=2)=[O:9])=[CH:4][CH:3]=1.[CH3:24][C:25]1[N:26]=[CH:27][NH:28][CH:29]=1.N1C=CC=CC=1C(=O)CC(C1C=CC=CN=1)=O.C([O-])([O-])=O.[Cs+].[Cs+]>[Cu]I.CN(C=O)C>[CH3:24][C:25]1[N:26]=[CH:27][N:28]([C:2]2[CH:23]=[CH:22][C:5]([CH2:6][NH:7][C:8]([C:10]3[CH:15]=[CH:14][C:13]([C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=4)=[CH:12][CH:11]=3)=[O:9])=[CH:4][CH:3]=2)[CH:29]=1

Komponenten

7

Edukt 4

HCID 10796Cesium carbonateHCID 27284941,3-Di(2-pyridyl)-1,3-propanedioneHCID 67208625N-(4-bromobenzyl)biphenyl-4-carboxamideHCID 178418800HCID 178418800, Verbindung

Produkt 1

HCID 66632643N-(4-(4-methyl-1H-imidazol-1-yl)benzyl)biphenyl-4-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

To a reaction vessel was added N-(4-bromobenzyl)biphenyl-4-carboxamide 10-3 (50 mg, 0.14 mmol), 4-methyl-1H-imidazole 11-1 (17 mg, 0.2 mmol), CuI (9 mg, 0.05 mmol), 1,3-di(pyridin-2-yl)propane-1,3-dione (15 mg, 0.07 mmol), Cs2CO3 (89 mg, 0.27 mmol) and DMF (0.7 mL). The reaction was flushed with nitrogen and stirred at 110° C. overnight. After cooling to room temperature, the reaction was diluted into ethyl acetate. The salt was removed by filtration and filtrate was dried. The residue was purified by HPLC to give N-(4-(4-methyl-1H-imidazol-1-yl)benzyl)biphenyl-4-carboxamide 92. MS m/z 368.2 (M+1). 1H NMR 400 MHz (DMSO-d6) δ 9.16 (t, 1H), 8.17 (s, 1H), 8.02 (d, 2H), 7.81 (d, 2H), 7.75 (d, 2H), 7.58 (d, 2H), 7.52-7.40 (m, 6H), 4.54 (d, 2H), 2.17 (s, 3H).

Aufarbeitung

  1. customThe reaction was flushed with nitrogen
  2. temperatureAfter cooling to room temperature
  3. additionthe reaction was diluted into ethyl acetate
  4. customThe salt was removed by filtration and filtrate
  5. customwas dried
  6. customThe residue was purified by HPLC

Quellen und Nachweise

ORD-Eintrag
ord-242b82d0d9dd490294bb460259101abe
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09181235B2

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