Water → 2-[2-Amino-4-(isoindoline-2-carbonyl)quinazolin-6-yl]-4-fluorobenzaldehyde

HRID 1631104Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1631104
Br[C:2]1[CH:9]=[C:8]([F:10])[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].C(=O)([O-])[O-].[K+].[K+].O.[NH2:18][C:19]1[N:28]=[C:27]([C:29]([N:31]2[CH2:39][C:38]3[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=3)[CH2:32]2)=[O:30])[C:26]2[C:21](=[CH:22][CH:23]=[C:24](B3OC(C)(C)C(C)(C)O3)[CH:25]=2)[N:20]=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]>[NH2:18][C:19]1[N:28]=[C:27]([C:29]([N:31]2[CH2:32][C:33]3[C:38](=[CH:37][CH:36]=[CH:35][CH:34]=3)[CH2:39]2)=[O:30])[C:26]2[C:21](=[CH:22][CH:23]=[C:24]([C:2]3[CH:9]=[C:8]([F:10])[CH:7]=[CH:6][C:3]=3[CH:4]=[O:5])[CH:25]=2)[N:20]=1

Komponenten

7

Edukt 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 27733192-Bromo-4-fluorobenzaldehydeHCID 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 867625702-[2-Amino-4-(isoindoline-2-carbonyl)quinazolin-6-yl]-4-fluorobenzaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 2

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

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

244 mg of 2-bromo-4-fluorobenzaldehyde, 0.35 g of potassium carbonate, 4 μl of water and 98 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 12 ml of ethanol under argon. The mixture is heated at 120° C. for 4 h; then allowed to cool, during which a precipitate deposits. The precipitate is filtered off, taken up in 10 ml of ethyl acetate and washed 3 times with 10 ml of water each time. After drying over sodium sulfate, the mixture is filtered off and evaporated to dryness in vacuo; yield: 495 mg (91%) of 2-[2-amino-4-(isoindoline-2-carbonyl)quinazolin-6-yl]-4-fluorobenzaldehyde; HPLC retention time: 1.73 min;

Aufarbeitung

  1. temperatureto cool, during which a precipitate deposits
  2. filtrationThe precipitate is filtered off
  3. washwashed 3 times with 10 ml of water each time
  4. dry with materialAfter drying over sodium sulfate
  5. filtrationthe mixture is filtered off
  6. customevaporated to dryness in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-d6f1bd01503a4835a5c210d89418a6ee
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08791129B2

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