Tetrahydrofuran → Methyl 1-methyl-3-phenyl-1H-indazole-6-carboxylate

HRID 1097000Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1097000
C1COCC1.I[C:7]1[C:15]2[C:10](=[CH:11][C:12]([C:16]([O:18][CH3:19])=[O:17])=[CH:13][CH:14]=2)[N:9]([CH3:20])[N:8]=1.[C:21]1(OB(O)O)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C([O-])([O-])=O.[K+].[K+]>C(OCC)(=O)C.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].O>[CH3:20][N:9]1[C:10]2[C:15](=[CH:14][CH:13]=[C:12]([C:16]([O:18][CH3:19])=[O:17])[CH:11]=2)[C:7]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[N:8]1

Komponenten

8

Edukt 4

HCID 8028TetrahydrofuranHCID 11430Potassium CarbonateHCID 78412Phenyl dihydrogen orthoborateHCID 57931017Methyl 3-iodo-1-methyl-1H-indazole-6-carboxylate

Produkt 1

HCID 57931013Methyl 1-methyl-3-phenyl-1H-indazole-6-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)KatalysatorHCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

In a 100-mL egg plant-type flask, PdCl2(dppf) (178 mg, 0.22 mmol) was added to a THF (20 mL)-water (2 mL) mixed solution of methyl 3-iodo-1-methyl-1H-indazole-6-carboxylate (690 mg, 22 mmol), phenylboric acid (399 mg, 3.27 mmol) and K2CO3 (1.35 g, 9.81 mmol), and stirred overnight at 80° C. in an argon atmosphere. This was diluted with ethyl acetate, washed with water and saturated saline water, dried with sodium sulfate, filtered and concentrated. The resulting crude product was purified through silica gel column chromatography to obtain the title compound.

Aufarbeitung

  1. washwashed with water and saturated saline water
  2. dry with materialdried with sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe resulting crude product was purified through silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-4b4c9fc9a98146f5bc846b0e8d5602d1
Quelldatensatz
uspto-grants-2012_03
Patentnummer
US08138197B2

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