Water → 6-[2-Amino-4-(isoindoline-2-carbonyl)quinazolin-6-yl]-1,3-benzodioxole-5-carbaldehyde

HRID 1631107Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1631107
Br[C:2]1[C:3]([CH:11]=[O:12])=[CH:4][C:5]2[O:9][CH2:8][O:7][C:6]=2[CH:10]=1.C(=O)([O-])[O-].[K+].[K+].O.[NH2:20][C:21]1[N:30]=[C:29]([C:31]([N:33]2[CH2:41][C:40]3[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=3)[CH2:34]2)=[O:32])[C:28]2[C:23](=[CH:24][CH:25]=[C:26](B3OC(C)(C)C(C)(C)O3)[CH:27]=2)[N:22]=1>C(O)C.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]>[NH2:20][C:21]1[N:30]=[C:29]([C:31]([N:33]2[CH2:34][C:35]3[C:40](=[CH:39][CH:38]=[CH:37][CH:36]=3)[CH2:41]2)=[O:32])[C:28]2[C:23](=[CH:24][CH:25]=[C:26]([C:2]3[C:3]([CH:11]=[O:12])=[CH:4][C:5]4[O:9][CH2:8][O:7][C:6]=4[CH:10]=3)[CH:27]=2)[N:22]=1

Komponenten

7

Edukt 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 950621,3-Benzodioxole-5-carboxaldehyde, 6-bromo-HCID 58457219[2-Amino-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinazolin-4-yl]-(1,3-dihydroisoindol-2-yl)methanone

Produkt 1

HCID 871741096-[2-Amino-4-(isoindoline-2-carbonyl)quinazolin-6-yl]-1,3-benzodioxole-5-carbaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)KatalysatorHCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

280 mg of 6-bromo-1,3-benzodioxole-5-carbaldehyde, 331 mg of potassium carbonate, 22 μl of water and 49 mg of [1,1′-bis(diphenylphosphino)ferrocene]-palladium(II) dichloride are added to a solution of 500 mg of [2-amino-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinazolin-4-yl]-(1,3-dihydroisoindol-2-yl)methanone in 50 ml of ethanol under argon. The mixture is heated at 120° C. for 4 h; the hot mixture is filtered through kieselguhr, and the filtrate is evaporated. The residue obtained was triturated with 2 ml of acetonitrile, and the precipitate formed was filtered off with suction.

Aufarbeitung

  1. filtrationthe hot mixture is filtered through kieselguhr
  2. customthe filtrate is evaporated
  3. customThe residue obtained
  4. customwas triturated with 2 ml of acetonitrile
  5. customthe precipitate formed
  6. filtrationwas filtered off with suction

Quellen und Nachweise

ORD-Eintrag
ord-586e1854e4b14244ac44f173912e7f4a
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08791129B2

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