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Ethyl 4-chloro-6-fluoroquinazoline-2-carboxylate → (4-Chloro-6-fluoroquinazolin-2-yl)(4-fluorophenyl)methanone

HRID 625799
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 625799
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([F:12])[CH:10]=2)[N:5]=[C:4]([C:13]([O:15]CC)=O)[N:3]=1.[F:18][C:19]1[CH:24]=[CH:23][C:22]([Mg]Br)=[CH:21][CH:20]=1.C1COCC1>C1COCC1>[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([F:12])[CH:10]=2)[N:5]=[C:4]([C:13]([C:22]2[CH:23]=[CH:24][C:19]([F:18])=[CH:20][CH:21]=2)=[O:15])[N:3]=1
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Komponenten

4

Edukt 2

HCID 86649062Ethyl 4-chloro-6-fluoroquinazoline-2-carboxylateHCID 178420690HCID 178420690, Verbindung

Produkt 1

HCID 86649063(4-Chloro-6-fluoroquinazolin-2-yl)(4-fluorophenyl)methanoneAusbeute 69,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
-40 °C

Versuchsvorschrift

To a stirred solution of ethyl 4-chloro-6-fluoroquinazoline-2-carboxylate (1.06 g, 4.5 mmol) in THF (15 mL) at −40° C., was added dropwise 1 M 4-fluorophenylmagnesium bromide/THF (5.85 mL, 5.85 mmol). The mixture was stirred at −40° C. for 2 h. The reaction was quenched by adding 0.5 N HCl at 0° C. and then the mixture was extracted with EtOAc (2×20 mL). The solid that precipitated from the combined organic layers was removed by filtration and the filtrate was washed with brine. The organic phase was dried over MgSO4, filtered, and concentrated under reduced pressure. The residue was purified by silica gel chromatography to afford (4-chloro-6-fluoroquinazolin-2-yl)(4-fluorophenyl)methanone as a solid (950 mg, 69%). 1H NMR (300 MHz, DMSO-d6) δ 8.32-8.36 (m, 1H), 8.13-8.21 (m, 4H), 7.43 (t, J=8.2 Hz, 2H); LC-MS (ESI) m/z 305 (M+H)+.

Aufarbeitung

  1. customThe reaction was quenched
  2. additionby adding 0.5 N HCl at 0° C.
  3. extractionthe mixture was extracted with EtOAc (2×20 mL)
  4. customThe solid that precipitated from the combined organic layers
  5. customwas removed by filtration
  6. washthe filtrate was washed with brine
  7. dry with materialThe organic phase was dried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customThe residue was purified by silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-c1ecfe3b3a2c4169a08d7e23fe9b3dc2
Quelldatensatz
uspto-grants-2016_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09308207B2

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