Reaktionsgleichung
N(C(C)C)C(C)C.C([Li])CCC.[Br:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([CH2:20][N:21]2[CH:25]=[CH:24][N:23]=[N:22]2)[N:15]=1.N1([CH2:35][OH:36])C2C=CC=CC=2N=N1>C1COCC1>[Br:13][C:14]1[N:15]=[C:16]([CH:20]([N:21]2[CH:25]=[CH:24][N:23]=[N:22]2)[CH2:35][OH:36])[CH:17]=[CH:18][CH:19]=1Komponenten
Reaktionsbedingungen
- Temperatur
- -20 °C
Versuchsvorschrift
A solution of i-Pr2NH (370 μL, 2.59 mmol) in THF (3.0 mL) was cooled to −20° C., and n-butyllithium (970 μL, 2.43 mmol) was added dropwise. After stirring for 15 minutes at −20° C., the colorless solution was cooled to −78° C. before adding 2-bromo-6-(1H-1,2,3-triazol-1-ylmethyl)pyridine (200 mg, 0.84 mmol) in THF (2.0 mL) dropwise over 30 minutes. After stirring for an additional 30 minutes at −78° C., 1H-benzotriazole-1-methanol (250 mg, 1.67 mmol) in THF (5.0 mL) was added dropwise over 25 minutes. The solution was stirred at −78° C. for 2 h. The reaction was quenched (while cold) with water and extracted with EtOAc (2×). The combined organic layers were washed with brine, dried (MgSO4), filtered, and evaporated. Flash chromatography (50-100% EtOAc/hexanes) afforded the title compound as a colorless oil.
Aufarbeitung
- temperaturethe colorless solution was cooled to −78° C.
- stirringAfter stirring for an additional 30 minutes at −78° C.
- stirringThe solution was stirred at −78° C. for 2 h
- customThe reaction was quenched (while cold) with water
- extractionextracted with EtOAc (2×)
- washThe combined organic layers were washed with brine
- dry with materialdried (MgSO4)
- filtrationfiltered
- customevaporated
Quellen und Nachweise
- ORD-Eintrag
- ord-673732d331854224bb29206900207b74
- Quelldatensatz
- uspto-grants-2013_02
- Patentnummer
- US08367706B2
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