Cesium carbonate → tert-Butyl 3-[3,5-dichlorophenyl)-1-[4-(methoxycarbonyl)benzyl]-1H-pyrazole-5-carboxylate

HRID 1865414Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1865414
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:13]=[C:12]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[NH:11][N:10]=2)[CH:5]=[C:6]([Cl:8])[CH:7]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:28][C:29]1[CH:38]=[CH:37][C:32]([C:33]([O:35][CH3:36])=[O:34])=[CH:31][CH:30]=1>CN(C)C=O.C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:13]=[C:12]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[N:11]([CH2:28][C:29]3[CH:30]=[CH:31][C:32]([C:33]([O:35][CH3:36])=[O:34])=[CH:37][CH:38]=3)[N:10]=2)[CH:5]=[C:6]([Cl:8])[CH:7]=1

Komponenten

6

Edukt 3

HCID 10796Cesium carbonateHCID 256687Methyl 4-(bromomethyl)benzoateHCID 86620042tert-Butyl 3-(3,5-dichlorophenyl)-1H-pyrazole-5-carboxylate

Produkt 1

HCID 86620043tert-Butyl 3-[3,5-dichlorophenyl)-1-[4-(methoxycarbonyl)benzyl]-1H-pyrazole-5-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of the product from step D (6.8 g, 21.7 mmol) in 50 mL of N,N-dimethylformamide was added cesium carbonate (10.6 g, 32.6 mmol) and the resultant mixture stirred at ambient temperature for 15 min. Methyl 4-(bromo-methyl)benzoate (5.46 g, 23.9 mmol) was added and stirring continued for 3 h. The reaction mixture was diluted with ethyl acetate and the organic layer washed successively with six portions of water and one portion of brine then dried over magnesium sulfate and concentrated in vacuo. The residue was purified by flash column chromatography (SiO2, 5% ethyl acetate/hexanes) to give the title compound as a light tan solid. 1H NMR (500 MHz, CDCl3) δ; 8.03 (d, J=8.4 Hz, 2H); 7.75 (d, J=1.8 Hz, 2H); 7.35 (m, 3H); 7.12 (s, 1H); 5.88 (s, 2H); 3.94 (s, 3H); 1.57 (s, 9H).

Aufarbeitung

  1. washthe organic layer washed successively with six portions of water and one portion of brine
  2. dry with materialthen dried over magnesium sulfate
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by flash column chromatography (SiO2, 5% ethyl acetate/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-560e428016964bfeb5432877c3595a7e
Quelldatensatz
uspto-grants-2009_12
Patentnummer
US07625938B2

Notizen zur Reaktion

Wird geladen…