Sodium Carbonate → HCID 59379869, Verbindung

HRID 2353730Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2353730
CC1(C)C(C)(C)OB([C:9]2[CH:15]=[CH:14][C:12]([NH2:13])=[CH:11][CH:10]=2)O1.Cl[C:18]1[N:23]=[C:22]([C:24]([S:27]([C:30]2[CH:35]=[CH:34][C:33]([F:36])=[CH:32][CH:31]=2)(=[O:29])=[O:28])([CH3:26])[CH3:25])[CH:21]=[C:20]([N:37]2[CH2:42][CH2:41][O:40][CH2:39][C@@H:38]2[CH3:43])[N:19]=1.C(=O)([O-])[O-].[Na+].[Na+]>CN(C=O)C.COCCOC.O.C(O)C.C(OCC)(=O)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[F:36][C:33]1[CH:34]=[CH:35][C:30]([S:27]([C:24]([C:22]2[CH:21]=[C:20]([N:37]3[CH2:42][CH2:41][O:40][CH2:39][C@@H:38]3[CH3:43])[N:19]=[C:18]([C:9]3[CH:10]=[CH:11][C:12]([NH2:13])=[CH:14][CH:15]=3)[N:23]=2)([CH3:26])[CH3:25])(=[O:28])=[O:29])=[CH:31][CH:32]=1

Komponenten

8

Edukt 3

HCID 10340Sodium CarbonateHCID 27346204-(Tetramethyl-1,3,2-dioxaborolan-2-yl)anilineHCID 59379876HCID 59379876, Verbindung

Produkt 1

HCID 59379869HCID 59379869, VerbindungAusbeute 79,2 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 178418476HCID 178418476, VerbindungKatalysatorHCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittelHCID 86587095Dimethoxyethane ethanol waterLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

Dichlorobis(triphenylphosphine)palladium(II) (170 mg, 0.24 mmol) was added to 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (1.376 g, 6.28 mmol) and 2-chloro-4-[2-(4-fluorophenyl)sulfonylpropan-2-yl]-6-[(3S)-3-methylmorpholin-4-yl]pyrimidine (2 g, 4.83 mmol), and sodium carbonate (5 mL, 10.00 mmol) in 18% DMF in DME:water:ethanol (7:3:2) (20 mL). The resulting solution was stirred at 90° C. for 4 hours. The reaction mixture was diluted with ethyl acetate (20 mL), and washed with water (2×20 mL1). The organic layer was dried (MgSO4), filtered and evaporated to afford crude product. The crude product was purified by flash silica chromatography, elution gradient 5 to 60% ethyl acetate in isohexane, to give the desired material as a cream solid (1.80 g).

Aufarbeitung

  1. washwashed with water (2×20 mL1)
  2. dry with materialThe organic layer was dried (MgSO4)
  3. filtrationfiltered
  4. customevaporated
  5. customto afford crude product
  6. customThe crude product was purified by flash silica chromatography, elution gradient 5 to 60% ethyl acetate in isohexane

Quellen und Nachweise

ORD-Eintrag
ord-3c2969fca3244ab59ac2c2714416fc6d
Quelldatensatz
uspto-grants-2010_07
Patentnummer
US07750003B2

Notizen zur Reaktion

Wird geladen…