1,1-Dibromoethane → 1-Bromo-3-[7-bromo-1-[(S)-2-(tert-butyl-dimethyl-silanyloxy)-propyl]-1H-indazol-6-yloxy]-propan-2-ol

HRID 1815963

Reaktionsgleichung

[Mg].[Br:2]C(Br)C.[Br:6][C:7]1[C:8]([O:27][CH2:28][CH:29]2[CH2:31][O:30]2)=[CH:9][CH:10]=[C:11]2[C:15]=1[N:14]([CH2:16][C@@H:17]([O:19][Si:20]([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21])[CH3:18])[N:13]=[CH:12]2>C1COCC1>[Br:2][CH2:31][CH:29]([OH:30])[CH2:28][O:27][C:8]1[C:7]([Br:6])=[C:15]2[C:11]([CH:12]=[N:13][N:14]2[CH2:16][C@@H:17]([O:19][Si:20]([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21])[CH3:18])=[CH:10][CH:9]=1

Komponenten

Reaktionsbedingungen

Temperatur: 50 °C

Versuchsvorschrift

To a suspension of magnesium powder (0.73 g, 30.2 mmol) in anhydrous THF (50 mL) under nitrogen was added dibromoethane (2.13 g, 0.98 mL, 11.3 mmol) in portions over about 30 min. During this period the mixture was heated at about 50° C. until gas evolution was observed. The mixture was stirred for an additional 1 h, placed in an ice bath, and a solution of the product from Step D (3.33 g, 7.55 mmol) in THF (10 mL) was added. After stirring for 1 h at ambient temperature, the mixture was quenched with a saturated aqueous solution of ammonium chloride (100 mL) and extracted with EtOAc (3×100 mL). Evaporation of the extracts gave a crude oil (3.76 g, 95%): LC/MS (+APCI) m/z 441, 443 (M+H−HBr).

Aufarbeitung

customplaced in an ice bath
stirringAfter stirring for 1 h at ambient temperature
customthe mixture was quenched with a saturated aqueous solution of ammonium chloride (100 mL)
extractionextracted with EtOAc (3×100 mL)
customEvaporation of the extracts

Quellen und Nachweise

ORD-Eintrag: ord-3ad693654e834867a58c503ce29cc182
Quelldatensatz: uspto-grants-2005_04
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US06881749B2

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