Ethyl 4-chloroquinazoline-2-carboxylate → HCID 86649047, Verbindung

HRID 625731

Reaktionsgleichung

Reaktionsgleichung von HRID 625731
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([C:12]([O:14]CC)=O)[N:3]=1.[F:17][C:18]1[CH:19]=[C:20]([Mg]Br)[CH:21]=[CH:22][CH:23]=1>C1COCC1>[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([C:12]([C:22]2[CH:21]=[CH:20][CH:19]=[C:18]([F:17])[CH:23]=2)=[O:14])[N:3]=1

Komponenten

4

Edukt 2

HCID 3477840Ethyl 4-chloroquinazoline-2-carboxylateHCID 178505773HCID 178505773, Verbindung

Produkt 1

HCID 86649047HCID 86649047, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
-20 °C

Versuchsvorschrift

To a suspension of ethyl 4-chloroquinazoline-2-carboxylate (237 mg, 1 mmol) in THF (5 mL) was added dropwise a 1M solution of 3-fluorophenylmagnesium bromide in THF (2 mL, 2 mmol) at −20° C. The reaction mixture was stirred at −20° C. for 4 h. The mixture was quenched by adding 0.5 N HCl solution (5 mL) and the biphasic mixture was extracted with EtOAc (2×10 mL). The combined organic layers were washed with brine and dried over MgSO4. (4-chloroquinazolin-2-yl)(3-fluorophenyl)methanone was obtained as a yellow solid (190 mg, 66%). LC-MS (ESI) m/z 287 (M+H)+.

Aufarbeitung

  1. customThe mixture was quenched
  2. additionby adding 0.5 N HCl solution (5 mL)
  3. extractionthe biphasic mixture was extracted with EtOAc (2×10 mL)
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over MgSO4

Quellen und Nachweise

ORD-Eintrag
ord-c9adf62b5e1e438681ce96cc49ff8919
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09308207B2

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