Potassium Phosphate, Tribasic → Ethyl 5-(4-methyl-3,5-diphenyl-1H-pyrazol-1-yl)thiophene-2-carboxylate

HRID 1671286

Reaktionsgleichung

Reaktionsgleichung von HRID 1671286
[C:1]1([C:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[NH:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].CN(C)[C@H:26]1[CH2:31]CCC[C@@H:27]1N.Br[C:35]1[S:39][C:38]([C:40]([O:42][CH2:43][CH3:44])=[O:41])=[CH:37][CH:36]=1>CN(C)C(=O)C.[Cu](I)I.O>[CH3:14][C:15]1[C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[N:8][N:9]([C:35]2[S:39][C:38]([C:40]([O:42][CH2:43][CH3:44])=[O:41])=[CH:37][CH:36]=2)[C:10]=1[C:11]1[CH:12]=[CH:13][CH:31]=[CH:26][CH:27]=1

Komponenten

8

Edukt 4

HCID 62657Potassium Phosphate, TribasicHCID 3003853-phenyl-1H-indazoleHCID 605723Ethyl 5-bromothiophene-2-carboxylateHCID 12188264(1S,2S)-N~1~,N~1~-Dimethylcyclohexane-1,2-diamine

Produkt 1

HCID 67059777Ethyl 5-(4-methyl-3,5-diphenyl-1H-pyrazol-1-yl)thiophene-2-carboxylateAusbeute 366,1 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 83717Copper iodideKatalysatorHCID 962WaterLösungsmittelHCID 31374DimethylacetamideLösungsmittel

Versuchsvorschrift

To a solution of 3-phenyl-1H-indazole (50 mg) synthesized according to the literature (T. Edward C., et al., Tetrahedron, 1991, 47, 9599-9620) in N,N-dimethylacetamide (500 μL, manufactured by Kanto Chemical Co., Inc.), potassium phosphate (85 mg, manufactured by Wako Pure Chemical Industries, Ltd.), (1S,2S)-(+)-N,N-dimethylcyclohexane-1,2-diamine (5 mg, manufactured by Tokyo Chemical Industry Co., Ltd.), copper iodide (4 mg, manufactured by Kanto Chemical Co., Inc.), and ethyl 5-bromothiophene-2-carboxylate (45 mg, manufactured by Alfa Aesar GmbH & Co. KG) were added, and the mixture was irradiated with microwave irradiation for 45 minutes at 185° C. The reaction solution was cooled to room temperature, and then water (1 mL) was added thereto. The mixture was extracted with ethyl acetate (3×2 mL), washed with brine (5 mL), and dried (MgSO4), and then the mixture was evaporated. The resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate 85:15), to give 50 mg of the title compound. LC-MS: HPLC retention time 6.52 minutes, m/z 349 (M+H), condition A-1.

Aufarbeitung

  1. customthe mixture was irradiated with microwave irradiation for 45 minutes at 185° C
  2. extractionThe mixture was extracted with ethyl acetate (3×2 mL)
  3. washwashed with brine (5 mL)
  4. dry with materialdried (MgSO4)
  5. customthe mixture was evaporated
  6. customThe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate 85:15)

Quellen und Nachweise

ORD-Eintrag
ord-16949cf47bf949269fba50c1a2374db3
Quelldatensatz
uspto-grants-2011_08
Patentnummer
US07994202B2

Verknüpfte Notizen

Wird geladen…