HCID 59251034, Verbindung → methyl 2-((1-(4-fluorophenyl)-1H-indazol-5-yl)(phenyl)methyl)pentanoate

HRID 218145Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 218145
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]3[C:11](=[CH:12][C:13]([CH:17]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)O)=[CH:14][CH:15]=3)[CH:10]=[N:9]2)=[CH:4][CH:3]=1.[CH3:25][O:26][C:27]([O:32][Si](C)(C)C)=[CH:28][CH2:29][CH2:30][CH3:31]>C(Cl)Cl.Cl[Ti](Cl)(Cl)Cl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]3[C:11](=[CH:12][C:13]([CH:17]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)[CH:28]([CH2:29][CH2:30][CH3:31])[C:27]([O:26][CH3:25])=[O:32])=[CH:14][CH:15]=3)[CH:10]=[N:9]2)=[CH:4][CH:3]=1

Komponenten

5

Edukt 2

HCID 59251034HCID 59251034, VerbindungHCID 71414635[(1-Methoxypent-1-en-1-yl)oxy](trimethyl)silane

Produkt 1

HCID 68706692methyl 2-((1-(4-fluorophenyl)-1H-indazol-5-yl)(phenyl)methyl)pentanoateAusbeute 77 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24193Titanium TetrachlorideKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of (1-(4-fluorophenyl)-1H-indazol-5-yl)(phenyl)methanol (158 mg, 0.5 mmol) and (1-methoxypent-1-enyloxy)trimethylsilane (16 mmol) which was prepared using General Silyl Ketene Acetal Method A in 10 mL of dry DCM was added TiCl4 (0.5 mL of 1.0 M DCM solution, 0.5 mmol) and then stirred 1 h. The reaction was quenched with MeOH, poured into aqueous sodium bicarbonate and extracted 2× EtOAc. The organic layers were dried over MgSO4, filtered, concentrated and purified on SiO2 by MPLC using a EtOAc/hexane gradient to give 160 mg (77% yield) of methyl 2-((1-(4-fluorophenyl)-1H-indazol-5-yl)(phenyl)methyl)pentanoate. MS found: (M+H)+=417.

Aufarbeitung

  1. customThe reaction was quenched with MeOH
  2. additionpoured into aqueous sodium bicarbonate
  3. extractionextracted 2× EtOAc
  4. dry with materialThe organic layers were dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. custompurified on SiO2 by MPLC

Quellen und Nachweise

ORD-Eintrag
ord-56a3e40d66d240e9a374524385f24fc0
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08198311B2

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