Potassium Phosphate, Tribasic → Ethyl 2-(3-phenyl-1H-indazol-1-yl)thiazole-4-carboxylate

HRID 1671284

Reaktionsgleichung

Reaktionsgleichung von HRID 1671284
[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]1CCCC[C@@H]1N.Br[C:35]1[S:36][CH:37]=[C:38]([C:40]([O:42][CH2:43][CH3:44])=[O:41])[N:39]=1>C1(C)C=C(C)C=C(C)C=1.[Cu](I)I.O>[C:1]1([C:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[N:9]([C:35]3[S:36][CH:37]=[C:38]([C:40]([O:42][CH2:43][CH3:44])=[O:41])[N:39]=3)[N:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Komponenten

8

Edukt 4

HCID 62657Potassium Phosphate, TribasicHCID 3003853-phenyl-1H-indazoleHCID 353965Ethyl 2-bromo-1,3-thiazole-4-carboxylateHCID 12188264(1S,2S)-N~1~,N~1~-Dimethylcyclohexane-1,2-diamine

Produkt 1

HCID 67059757Ethyl 2-(3-phenyl-1H-indazol-1-yl)thiazole-4-carboxylateAusbeute 46,7 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 83717Copper iodideKatalysatorHCID 962WaterLösungsmittelHCID 7947MesityleneLösungsmittel

Reaktionsbedingungen

Temperatur
180 °C

Versuchsvorschrift

To a solution of 3-phenyl-1H-indazole (689 mg) synthesized according to the literature (T. Edward C., et al., Tetrahedron, 1991, 47, 9599-9620) in mesitylene (5 mL, manufactured by Kanto Chemical Co., Inc.), potassium phosphate (2.38 g, manufactured by Wako Pure Chemical Industries, Ltd.), (1S,2S)-(+)-N,N-dimethylcyclohexane-1,2-diamine (50 mg, manufactured by Tokyo Chemical Industry Co., Ltd.), copper iodide (34 mg, manufactured by Kanto Chemical Co., Inc.), and ethyl 2-bromo-4-thiazolecarboxylate (840 mg) synthesized according to the literature (T. R. Kelly, et al., J. Org. Chem., 1996, 61, 4623-4633) were added, and the mixture was heated overnight at 180° C. The reaction solution was cooled to room temperature, and then water (20 mL) was added thereto. Ethyl acetate was extracted (3×20 mL), washed with brine (20 mL), and dried (MgSO4), and then the solvent was evaporated. The resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1), to give 579 mg of the title compound. LC-MS: HPLC retention time 6.80 minutes, m/z 350 (M+H), condition B-1.

Aufarbeitung

  1. addition, 1996, 61, 4623-4633) were added
  2. temperatureThe reaction solution was cooled to room temperature
  3. extractionEthyl acetate was extracted (3×20 mL)
  4. washwashed with brine (20 mL)
  5. dry with materialdried (MgSO4)
  6. customthe solvent was evaporated
  7. customThe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1)

Quellen und Nachweise

ORD-Eintrag
ord-911d0b0efb7e4626a93837a4f8addc20
Quelldatensatz
uspto-grants-2011_08
Patentnummer
US07994202B2

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