Triethylamine → 1h-Indazole-1-carboxylic acid,5-(chloromethyl)-3-(3-fluorophenyl)-,1,1-dimethylethyl ester

HRID 503119Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 503119
[F:1][C:2]1[CH:3]=[C:4]([C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([CH2:17]O)[CH:15]=3)[N:10]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[N:9]=2)[CH:5]=[CH:6][CH:7]=1.C(N(CC)CC)C.CS([Cl:37])(=O)=O.C(OCC)(=O)C>C(Cl)Cl>[Cl:37][CH2:17][C:14]1[CH:15]=[C:16]2[C:11](=[CH:12][CH:13]=1)[N:10]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[N:9]=[C:8]2[C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[CH:3]=1

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 31297Methanesulfonyl chlorideHCID 222608021h-Indazole-1-carboxylic acid,3-(3-fluorophenyl)-5-(hydroxymethyl)-,1,1-dimethylethyl ester

Produkt 1

HCID 222606161h-Indazole-1-carboxylic acid,5-(chloromethyl)-3-(3-fluorophenyl)-,1,1-dimethylethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Under ice-cooling, to a solution of 3.0 g of tert-butyl 3-(3-fluorophenyl)-5-(hydroxymethyl)-1H-1-indazolecarboxylate in 30 ml methylene chloride were added 1.6 ml of triethylamine and 0.78 ml of methanesulfonyl chloride, and the mixture was stirred at room temperature for one day. To the reaction mixture was added 180 ml of ethyl acetate, and the mixture was sequentially washed with water, 1 N hydrochloric acid, water, saturated aqueous sodium hydrogencarbonate solution and brine, dried over anhydrous magnesium sulfate and the solvent was evaporated. The crude product was purified and separated by silica gel column chromatography (toluene), to give 2.74 g of the title compound as yellow crystals.

Aufarbeitung

  1. washthe mixture was sequentially washed with water, 1 N hydrochloric acid, water, saturated aqueous sodium hydrogencarbonate solution and brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customthe solvent was evaporated
  4. customThe crude product was purified
  5. customseparated by silica gel column chromatography (toluene)

Quellen und Nachweise

ORD-Eintrag
ord-b836823401be4d4e9afda0304d2f8678
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07776890B2

Notizen zur Reaktion

Wird geladen…