Water → 2-{(3-phenyl-1H-indazol-1-yl)methyl}thiazole-4-carboxylic acid

HRID 1671290Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1671290
[H-].[Na+].[C:3]1([C:9]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[NH:11][N:10]=2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Br[CH2:19][C:20]1[S:21][CH:22]=[C:23]([C:25]([O:27]CC)=[O:26])[N:24]=1.O>CN(C)C=O>[C:3]1([C:9]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[N:11]([CH2:19][C:20]3[S:21][CH:22]=[C:23]([C:25]([OH:27])=[O:26])[N:24]=3)[N:10]=2)[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 24758Sodium hydrideHCID 3003853-phenyl-1H-indazoleHCID 11043146Ethyl 2-(bromomethyl)-1,3-thiazole-4-carboxylate

Produkt 1

HCID 670597712-{(3-phenyl-1H-indazol-1-yl)methyl}thiazole-4-carboxylic acidAusbeute 10,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Sodium hydride (added with 40% mineral oil, 9 mg, manufactured by Kanto Chemical Co., Inc.) was added to a solution of 3-phenyl-1H-indazole (40 mg), which had been synthesized according to the literature (T. Edward, C., et al., Tetrahedron, 1991, 47, 9599-9620), in N,N-dimethylformamide (1 mL, manufactured by Kanto Chemical Co., Inc.) under ice cooling, and the mixture was stirred for 5 minutes at the same temperature. Subsequently, ethyl 2-bromomethylthiazole-4-carboxylate (51 mg) synthesized according to the method of the literature (K. Benno, et al., Leibigs. Ann. Chem., 1981, 4, 623-632) was added thereto, and the mixture was stirred overnight at room temperature. Water (1 mL) was added to the reaction solution, and the mixture was extracted with ethyl acetate (3×2 mL), washed with brine (10 mL), and dried (MgSO4). The solvent was then evaporated. The resulting residue was purified by PTLC (hexane:ethyl acetate=2:1), to give 7.2 mg of the title compound. LC-MS: HPLC retention time 4.08 minutes, m/z 336 (M+H), condition A-1.

Aufarbeitung

  1. customhad been synthesized
  2. additionwas added
  3. stirringthe mixture was stirred overnight at room temperature
  4. extractionthe mixture was extracted with ethyl acetate (3×2 mL)
  5. washwashed with brine (10 mL)
  6. dry with materialdried (MgSO4)
  7. customThe solvent was then evaporated
  8. customThe resulting residue was purified by PTLC (hexane:ethyl acetate=2:1)

Quellen und Nachweise

ORD-Eintrag
ord-bc99c131f50e46f482ba51bc7f7a5a00
Quelldatensatz
uspto-grants-2011_08
Patentnummer
US07994202B2

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