N-bromobutanimide → 7-Bromo-1-[(S)-2-(tert-butyldimethyl-silanyloxy)-propyl]-1H-indazol-6-ol

HRID 1815961

Reaktionsgleichung

Reaktionsgleichung von HRID 1815961
[C:1]([Si:5]([CH3:21])([CH3:20])[O:6][C@@H:7]([CH3:19])[CH2:8][N:9]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([OH:18])[CH:16]=2)[CH:11]=[N:10]1)([CH3:4])([CH3:3])[CH3:2].[Br:22]N1C(=O)CCC1=O.S(=O)(O)[O-].[Na+]>C1COCC1>[Br:22][C:16]1[C:15]([OH:18])=[CH:14][CH:13]=[C:12]2[C:17]=1[N:9]([CH2:8][C@@H:7]([O:6][Si:5]([C:1]([CH3:3])([CH3:4])[CH3:2])([CH3:21])[CH3:20])[CH3:19])[N:10]=[CH:11]2

Komponenten

5

Edukt 3

HCID 67184N-bromobutanimideHCID 23665763Sodium BisulfiteHCID 1364116801-[(S)-2-(tert-Butyldimethyl-silanyloxy)-propyl]-1H-indazol-6-ol

Produkt 1

HCID 1364116817-Bromo-1-[(S)-2-(tert-butyldimethyl-silanyloxy)-propyl]-1H-indazol-6-olAusbeute 77 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of the product from Step B (3.79 g, 12.4 mmol) in anhydrous THF (100 mL) at 0° C. was added N-bromosuccinimide (2.20 g, 12.4 mmol) in 3 portions over 10 min. After 20 min the mixture was poured into a saturated aqueous solution of sodium bisulfite (100 mL) and extracted with EtOAc (3×200 mL). The combined extracts were dried (MgSO4) and evaporated to a residue (4.79 g). Chromatography (silica, 10% EtOAc/hexane) gave a solid (3.66 g, 77%): mp 103-105° C.

Aufarbeitung

  1. extractionextracted with EtOAc (3×200 mL)
  2. dry with materialThe combined extracts were dried (MgSO4)
  3. customevaporated to a residue (4.79 g)

Quellen und Nachweise

ORD-Eintrag
ord-84a24f4e58d542c98312fd1bd110f047
Quelldatensatz
uspto-grants-2005_04
Patentnummer
US06881749B2

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