Sodium Iodide → 6-Benzyloxy-1-[(S)-2-(tert-butyldimethyl-silanyloxy)-propyl]-1H-indazole

HRID 2121881

Reaktionsgleichung

Reaktionsgleichung von HRID 2121881
[CH2:1]([O:8][C:9]1[CH:17]=[C:16]2[C:12]([CH:13]=[N:14][N:15]2[CH2:18][C@@H:19]([OH:21])[CH3:20])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[C:24]([Si:28](Cl)([CH3:30])[CH3:29])([CH3:27])([CH3:26])[CH3:25].[Na+].[I-]>C1COCC1.CN(C=O)C>[CH2:1]([O:8][C:9]1[CH:17]=[C:16]2[C:12]([CH:13]=[N:14][N:15]2[CH2:18][C@@H:19]([O:21][Si:28]([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:30])[CH3:29])[CH3:20])=[CH:11][CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

6

Edukt 4

HCID 5238Sodium IodideHCID 24758Sodium hydride2×HCID 28928tert-Butyldimethylsilyl chloride2×HCID 11659201(S)-1-(6-Benzyloxyindazol-1-yl)-propan-2-ol

Produkt 1

HCID 695717436-Benzyloxy-1-[(S)-2-(tert-butyldimethyl-silanyloxy)-propyl]-1H-indazoleAusbeute 99 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21974620tetrahydrofuran N,N-dimethylformamideLösungsmittel

Versuchsvorschrift

To a mixture of (S)-1-(6-benzyloxyindazol-1-yl)-propan-2-ol (2.03 g, 7.20 mmol) in anhydrous THF/DMF (100 mL/35 mL) under nitrogen was added sodium hydride (60% in mineral oil, 0.40 g, 10.0 mmol). After 30 min tert-butyl-chloro-dimethyl-silane (1.52 g, 110 mmol) and a catalytic amount of NaI were added and the mixture was stirred overnight at ambient temperature. Additional NaH (5 mmol) and tert-butyl-chloro-dimethyl-silane (5 mmol) were added to the reaction mixture, which was stirred for 6 h. The reaction mixture was evaporated to a residue that was mixed with a saturated aqueous solution of sodium bicarbonate and extracted with ethyl acetate (2×200 mL). Purification by chromatography (silica, EtOAc/hexane) gave an oil (2.81 g, 99%).

Aufarbeitung

  1. stirringwas stirred for 6 h
  2. customThe reaction mixture was evaporated to a residue that
  3. additionwas mixed with a saturated aqueous solution of sodium bicarbonate
  4. extractionextracted with ethyl acetate (2×200 mL)
  5. customPurification by chromatography (silica, EtOAc/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-efb99e2b8a90486e95d1b534b71a8857
Quelldatensatz
uspto-grants-2004_02
Patentnummer
US06696476B2

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