Water → 4-(7-Bromo-2-methylquinazolin-4-YL)-3-methoxybenzonitrile

HRID 1473679Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1473679
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1B1OC(C)(C)C(C)(C)O1)[C:6]#[N:7].[Br:20][C:21]1[CH:30]=[C:29]2[C:24]([C:25](Cl)=[N:26][C:27]([CH3:31])=[N:28]2)=[CH:23][CH:22]=1.C(=O)([O-])[O-].[K+].[K+].O>O1CCOCC1.C(Cl)Cl.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].C(Cl)Cl>[Br:20][C:21]1[CH:30]=[C:29]2[C:24]([C:25]([C:10]3[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=3[O:2][CH3:1])=[N:26][C:27]([CH3:31])=[N:28]2)=[CH:23][CH:22]=1

Komponenten

8

Edukt 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 222478197-Bromo-4-chloro-2-methylquinazolineHCID 689291003-Methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile

Produkt 1

HCID 866877614-(7-Bromo-2-methylquinazolin-4-YL)-3-methoxybenzonitrile

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418807HCID 178418807, VerbindungKatalysatorHCID 6344DichloromethaneLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

A solution of PdCl2(dppf)-CH2Cl2 adduct (0.072 g, 0.088 mmol), 3-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile (Intermediate GGGG) (0.500 g, 1.930 mmol), 7-bromo-4-chloro-2-methylquinazoline (0.452 g, 1.754 mmol), and potassium carbonate (0.970 g, 7.02 mmol) in 3 mL dioxane was treated with 1 mL water and was allowed to stir at room temperature 3 hours. LC/MS showed mostly product, so the reaction mixture was diluted with DCM and washed with water. The aqueous layer was removed and the reaction mixture was concentrated. The crude residue was carried forward to step 2 without purification. (M+H)+=354.0.

Aufarbeitung

  1. washwashed with water
  2. customThe aqueous layer was removed
  3. concentrationthe reaction mixture was concentrated
  4. customThe crude residue was carried forward to step 2 without purification

Quellen und Nachweise

ORD-Eintrag
ord-dfb36f21679643629f21d398277fb788
Quelldatensatz
uspto-grants-2015_04
Patentnummer
US09012443B2

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