Potassium Phosphate, Tribasic → HCID 71008519, Verbindung

HRID 1025560Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1025560
Br[C:2]1[O:6][C:5]([C:7]([NH2:9])=[O:8])=[CH:4][CH:3]=1.[C:10]([C:14]1[CH:15]=[C:16]2[C:21](=[C:22]([F:24])[CH:23]=1)[C:20](=[O:25])[N:19]([C:26]1[CH:36]=[CH:35][CH:34]=[C:33](B3OC(C)(C)C(C)(C)O3)[C:27]=1[CH2:28][O:29][C:30](=[O:32])[CH3:31])[N:18]=[CH:17]2)([CH3:13])([CH3:12])[CH3:11].CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>O1CCOCC1.O.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[C:10]([C:14]1[CH:15]=[C:16]2[C:21](=[C:22]([F:24])[CH:23]=1)[C:20](=[O:25])[N:19]([C:26]1[CH:36]=[CH:35][CH:34]=[C:33]([C:2]3[O:6][C:5]([C:7](=[O:8])[NH2:9])=[CH:4][CH:3]=3)[C:27]=1[CH2:28][O:29][C:30](=[O:32])[CH3:31])[N:18]=[CH:17]2)([CH3:11])([CH3:12])[CH3:13]

Komponenten

8

Edukt 4

HCID 62657Potassium Phosphate, TribasicHCID 2335815-Bromofuran-2-carboxamideHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 594737692-(6-(tert-Butyl)-8-fluoro-1-oxophthalazin-2(1H)-yl)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl acetate

Produkt 1

HCID 71008519HCID 71008519, VerbindungAusbeute 16 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 962WaterLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

In a microwave flask, a suspension of 5-bromofuran-2-carboxamide (200 mg, 1.05 mmol), acetic acid 2-(6-tert-butyl-8-fluoro-1-oxo-1H-phthalazin-2-yl)-6-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzyl ester (Intermediate-5, 1.04 g, 2.11 mmol), X-PHOS (50.2 mg, 0.105 mmol), Pd2(dba)3 (48.2 mg, 0.052 mmol) and potassium phosphate (894 mg, 4.21 mmol) in dioxane (7 ml) and water (0.7 ml) was degassed with argon for 3-5 min. The mixture was set in a microwave at 125° C. for 30 min. Water was added and the mixture was extracted with ethyl acetate twice. The organic layer was washed with brine, dried over sodium sulfate and evaporated to dryness. The crude material was purified by flash column chromatography (ethyl acetate in hexanes, gradient to 100% ethyl acetate) to obtain acetic acid 2-(6-tert-butyl-8-fluoro-1-oxo-1H-phthalazin-2-yl)-6-(5-carbamoyl-furan-2-yl)-benzyl ester (78.5 mg, 16%).

Aufarbeitung

  1. customwas degassed with argon for 3-5 min
  2. additionWater was added
  3. extractionthe mixture was extracted with ethyl acetate twice
  4. washThe organic layer was washed with brine
  5. dry with materialdried over sodium sulfate
  6. customevaporated to dryness
  7. customThe crude material was purified by flash column chromatography (ethyl acetate in hexanes, gradient to 100% ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-fd590262c0254b4d9cfdbac99e287954
Quelldatensatz
uspto-grants-2014_05
Patentnummer
US08729078B2

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