Lithium diisopropylamide → 7-bromo-3-chloro-1-fluoro-5H-chromeno[2,3-c]pyridin-5-one

HRID 529426Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 529426
[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.O1CCCC1.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

HCID 2724682Lithium diisopropylamideHCID 22742125Tetrahydrofuran heptane ethylbenzolHCID 86640732HCID 86640732, Verbindung

Produkt 1

HCID 574756427-bromo-3-chloro-1-fluoro-5H-chromeno[2,3-c]pyridin-5-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

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, 2.0 m heptane/tetrahydrofuran/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

  1. customThe reaction was quenched at −78° C. with sat. NH4Cl
  2. temperatureto warm up to RT
  3. extractionThe reaction was extracted with ETOAc
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customevaporated to dryness
  7. customThe crude was purified by column chromatography (1:1 hexane/DCM to 100% DCM)

Quellen und Nachweise

ORD-Eintrag
ord-5a812b6f417741a284e3e53e026f6a41
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09346827B2

Notizen zur Reaktion

Wird geladen…