Lithium diisopropylamide → 7-bromo-3-chloro-1-fluoro-5H-chromeno[2,3-c]pyridin-5-one
Reaktionsgleichung
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:15][C:16]2[C:17]([F:23])=[N:18][C:19]([Cl:22])=[CH:20][CH:21]=2)=[C:6]([CH:14]=1)[C:7](N(CC)CC)=[O:8].C([N-]C(C)C)(C)C.[Li+].CCCCCCC.C1COCC1.C(C1C=CC=CC=1)C>C1COCC1>[Br:1][C:2]1[CH:14]=[C:6]2[C:5](=[CH:4][CH:3]=1)[O:15][C:16]1[C:17]([F:23])=[N:18][C:19]([Cl:22])=[CH:20][C:21]=1[C:7]2=[O:8]Komponenten
5
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- -78 °C
Versuchsvorschrift
To a solution of 5-bromo-2-(6-chloro-2-fluoropyridin-3-yloxy)-N,N-diethylbenzamide (120 mg, 0.299 mmol) in 5 mL of dry THF at −78° C. was added dropwise lithium diisopropylamide, 2.0M heptane/THF/ethylbenzene (158 μL, 1.195 mmol) (0.6 mL of 2M solution) and the reaction was stirred at −78° C. for 3 h. The reaction was quenched at −78° C. with sat. NH4Cl and was allowed to warm up to RT. The reaction was extracted with ETOAc, dried over Na2SO4, filtered and evaporated to dryness. The crude was purified by column chromatography (1:1 hexane/DCM to 100% DCM) to give the titled compound, 7-bromo-3-chloro-1-fluoro-5H-chromeno[2,3-c]pyridin-5-one, as an offwhite solid. MS (M+1): 328.
Aufarbeitung
- customThe reaction was quenched at −78° C. with sat. NH4Cl
- temperatureto warm up to RT
- extractionThe reaction was extracted with ETOAc
- dry with materialdried over Na2SO4
- filtrationfiltered
- customevaporated to dryness
- customThe crude was purified by column chromatography (1:1 hexane/DCM to 100% DCM)
Quellen und Nachweise
- ORD-Eintrag
- ord-292ef61033a547029fd7f788d58d8c3a
- Quelldatensatz
- uspto-grants-2015_02
- Patentnummer
- US08962859B2
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