2-Methoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane → 1-(3-{[tert-butyl(dimethyl)silyl]oxy}cyclobutyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole

HRID 1947843Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1947843
C([Mg]Cl)(C)C.[C:6]([Si:10]([CH3:23])([CH3:22])[O:11][CH:12]1[CH2:15][CH:14]([N:16]2[CH:20]=[C:19](I)[CH:18]=[N:17]2)[CH2:13]1)([CH3:9])([CH3:8])[CH3:7].CO[B:26]1[O:30][C:29]([CH3:32])([CH3:31])[C:28]([CH3:34])([CH3:33])[O:27]1>C1COCC1>[Si:10]([O:11][CH:12]1[CH2:15][CH:14]([N:16]2[CH:20]=[C:19]([B:26]3[O:30][C:29]([CH3:32])([CH3:31])[C:28]([CH3:34])([CH3:33])[O:27]3)[CH:18]=[N:17]2)[CH2:13]1)([C:6]([CH3:9])([CH3:8])[CH3:7])([CH3:23])[CH3:22]

Komponenten

5

Edukt 3

HCID 109757592-Methoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 672531081-[3-(tert-butyl-dimethyl-silanyloxy)-cyclobutyl]-4-iodo-1H-pyrazole2×HCID 178418918HCID 178418918, Verbindung

Produkt 1

HCID 672540531-(3-{[tert-butyl(dimethyl)silyl]oxy}cyclobutyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Over the course of 5 minutes, a 2.00 M solution of isopropylmagnesium chloride in THF (0.13084 mL, 0.26168 mmol) was added dropwise to an ice cooled solution of 1-[3-(tert-butyl-dimethyl-silanyloxy)-cyclobutyl]-4-iodo-1H-pyrazole (Compound 100B, 30.00 mg, 0.07930 mmol) in THF (0.33 mL). The reaction mixture was stirred at 0° C. for another hour. 2-Methoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (0.057933 mL, 0.33939 mmol) was added at 0° C. and then the mixture was stirred at rt for another hour. The reaction mixture was cooled back down to 0° C., quenched with saturated aqueous NH4Cl, and extracted with EtOAc. The combined organic layers were washed with brine, dried over anhydrous Na2SO4, filtered, and concentrated in vacuo to dryness, giving the title compound as a colorless oil. Compound was taken on for the next step without further purification. MS (ES+): m/z 379.04 (100) [MH+]; HPLC: tR=3.85 min (ZQ3, polar—5 min).

Aufarbeitung

  1. stirringthe mixture was stirred at rt for another hour
  2. temperatureThe reaction mixture was cooled back down to 0° C.
  3. customquenched with saturated aqueous NH4Cl
  4. extractionextracted with EtOAc
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over anhydrous Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo to dryness

Quellen und Nachweise

ORD-Eintrag
ord-713880fd79474db1815935a535451272
Quelldatensatz
uspto-grants-2013_03
Patentnummer
US08399433B2

Notizen zur Reaktion

Wird geladen…