Potassium Carbonate → HCID 66576591, Verbindung

HRID 1405192Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1405192
Cl[C:2]1[N:7]=[CH:6][N:5]=[C:4]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][S:16]([CH3:19])(=[O:18])=[O:17])[CH:10]=2)[N:3]=1.[Cl:20][C:21]1[CH:26]=[CH:25][C:24](B(O)O)=[C:23]([O:30][CH:31]2[CH2:35][CH2:34][CH2:33][CH2:32]2)[CH:22]=1.C(=O)([O-])[O-].[K+].[K+]>COCCOC.C(OCC)(=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]>[Cl:20][C:21]1[CH:26]=[CH:25][C:24]([C:2]2[N:7]=[CH:6][N:5]=[C:4]([NH:8][C:9]3[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][S:16]([CH3:19])(=[O:18])=[O:17])[CH:10]=3)[N:3]=2)=[C:23]([O:30][CH:31]2[CH2:35][CH2:34][CH2:33][CH2:32]2)[CH:22]=1

Komponenten

7

Edukt 3

HCID 11430Potassium CarbonateHCID 219563434-chloro-N-{3-[(methylsulfonyl)methyl]phenyl}-1,3,5-triazin-2-amineHCID 53216478[4-Chloro-2-(cyclopentyloxy)phenyl]boronic acid

Produkt 1

HCID 66576591HCID 66576591, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 44119782Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)KatalysatorHCID 80711,2-DimethoxyethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A batch with crude crude 4-chloro-N-{3-[(methylsulfonyl)methyl]phenyl}-1,3,5-triazin-2-amine (175 mg), [4-chloro-2-(cyclopentyloxy)phenyl]boronic acid (141 mg; 0.59 mmol; Combi-Blocks Inc.) and [1,1′-bis(diphenylphosphino)ferrocene]palladium dichloride (72 mg; 0.09 mmol) in 1,2-dimethoxyethane (2.0 mL) and 2M solution of potassium carbonate (0.6 mL) was degassed using argon. The batch was stirred under argon for 60 minutes at 100° C. After cooling the batch was diluted with ethyl acetate. The organic phase was filtered using a Whatman filter and concentrated. The residue was purified by preparative HPLC.

Aufarbeitung

  1. temperatureAfter cooling the batch
  2. filtrationThe organic phase was filtered
  3. filtrationfilter
  4. concentrationconcentrated
  5. customThe residue was purified by preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-21d4568740ff4bc0a104e5fa4bfc9e77
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08916557B2

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