1,2-Dibromoethane → Methyl 1-(quinolin-6-yl)cyclopropanecarboxylate
Reaktionsgleichung
[Li+].[CH3:2][CH:3]([N-]C(C)C)C.[CH3:9][O:10][C:11](=[O:23])[CH2:12][C:13]1[CH:14]=[C:15]2[C:20](=[CH:21][CH:22]=1)[N:19]=[CH:18][CH:17]=[CH:16]2.BrCCBr>C1COCC1>[N:19]1[C:20]2[C:15](=[CH:14][C:13]([C:12]3([C:11]([O:10][CH3:9])=[O:23])[CH2:3][CH2:2]3)=[CH:22][CH:21]=2)[CH:16]=[CH:17][CH:18]=1Komponenten
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
LDA (1.8 M solution in toluene, 14.8 mL, 26.6 mmol) was added dropwise to a solution of quinolin-6-yl-acetic acid methyl ester (2.14 g, 10.64 mmol) in dry THF (40 mL) under nitrogen at −78° C. After 30 min, 1,2-dibromoethane (2.40 g, 12.76 mmol) was added dropwise over 3 min. The resulting mixture was stirred for 1 h at rt, then quenched with saturated aqueous NH4Cl, extracted with DCM, washed with brine, dried over Na2SO4, and evaporated under reduced pressure. The residue was purified by flash chromatography on silica gel eluting with EtOAc/hexane gradient to afford the title compound as a yellow solid (463 mg, 20%). 1H-NMR (400 MHz, CDCl3) δ ppm 8.91 (dd, 1H), 8.12 (d, 1H), 8.07 (d, 1H), 7.77-7.74 (m, 2H), 7.40 (dd, 1H), 3.65 (s, 3H), 1.73-1.71 (m, 2H), 1.33-1.30 (m, 2H). LCMS (method A): [MH]+=228, tR=4.37 min.
Aufarbeitung
- customquenched with saturated aqueous NH4Cl
- extractionextracted with DCM
- washwashed with brine
- dry with materialdried over Na2SO4
- customevaporated under reduced pressure
- customThe residue was purified by flash chromatography on silica gel eluting with EtOAc/hexane gradient
Quellen und Nachweise
- ORD-Eintrag
- ord-c437f11fab0c4970a2e74fb30a8f4e68
- Quelldatensatz
- uspto-grants-2013_08
- Patentnummer
- US08507676B2
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