Triethyl borate → 3-[(tert-Butoxycarbonyl)amino]-2-(methylsulfanyl)pyrazolo[1,5-a]pyridin-7-ylboric Acid

HRID 9196

Reaktionsgleichung

I[C:2]1[N:7]2[N:8]=[C:9]([S:19][CH3:20])[C:10]([NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[C:6]2[CH:5]=[CH:4][CH:3]=1.C([Li])CCC.C([O:28][B:29]([O:33]CC)[O:30]CC)C.[Cl-].[NH4+]>O1CCCC1.C(OCC)(=O)C>[C:14]([O:13][C:12]([NH:11][C:10]1[C:9]([S:19][CH3:20])=[N:8][N:7]2[C:2]([O:28][B:29]([OH:33])[OH:30])=[CH:3][CH:4]=[CH:5][C:6]=12)=[O:18])([CH3:17])([CH3:16])[CH3:15]

Komponenten

Reaktionsbedingungen

Temperatur: -78 °C

Versuchsvorschrift

After dissolving tert-butyl N-(7-iodo-2-(methylsulfanyl)pyrazolo[1,5-a]pyridin-3-yl)carbamate (200 mg) in tetrahydrofuran (2 mL), the mixture was cooled to −78° C. and n-butyllithium (1.6 M; 0.66 mL) was added dropwise. The mixture was stirred for 1-hour at the same temperature, triethoxyborane (109 μL) was added and the temperature was increased to room temperature. Saturated aqueous ammonium chloride was added to the obtained reaction mixture, and extraction was performed with ethyl acetate. The obtained organic layer was washed with brine and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure to obtain the title compound (106 mg) as grayish white crystals.

Aufarbeitung

additionwas added
temperaturethe temperature was increased to room temperature
washThe obtained organic layer was washed with brine
dry with materialdried over anhydrous magnesium sulfate
distillationthe solvent was distilled off under reduced pressure

Quellen und Nachweise

ORD-Eintrag: ord-f6b1679482d14db0b11eddb742d1b067
Quelldatensatz: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07091215B2

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