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Potassium Phosphate, Tribasic → Ethyl 2-[6-{1-[(1,1-dimethylethyl)(dimethyl)silyl]-1H-indol-4-yl}-1-(phenylsulfonyl)-1H-indazol-4-yl]-1,3-oxazole-5-carboxylate

HRID 2042663
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2042663
Cl[C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[N:7][N:8]2[S:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)(=[O:13])=[O:12])=[C:4]([C:20]2[O:21][C:22]([C:25]([O:27][CH2:28][CH3:29])=[O:26])=[CH:23][N:24]=2)[CH:3]=1.[CH3:30][C:31]([Si:34]([CH3:48])([CH3:47])[N:35]1[C:43]2[C:38](=[C:39](B(O)O)[CH:40]=[CH:41][CH:42]=2)[CH:37]=[CH:36]1)([CH3:33])[CH3:32].[O-]P([O-])([O-])=O.[K+].[K+].[K+]>O1CCOCC1.O.Cl[Pd]C1C=CC=CC=1C1C=CC=CC=1N(C)C.[C@H]12C[C@H](CC1)CC2PC1C[C@H]2C[C@@H]1CC2>[CH3:33][C:31]([Si:34]([CH3:48])([CH3:47])[N:35]1[C:43]2[C:38](=[C:39]([C:2]3[CH:10]=[C:9]4[C:5]([CH:6]=[N:7][N:8]4[S:11]([C:14]4[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=4)(=[O:13])=[O:12])=[C:4]([C:20]4[O:21][C:22]([C:25]([O:27][CH2:28][CH3:29])=[O:26])=[CH:23][N:24]=4)[CH:3]=3)[CH:40]=[CH:41][CH:42]=2)[CH:37]=[CH:36]1)([CH3:30])[CH3:32]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 3

HCID 62657Potassium Phosphate, TribasicHCID 223523971-(tert-Butyldimethylsilyl)-1H-indole-4-boronic acidHCID 59564714HCID 59564714, Verbindung

Produkt 1

HCID 59564707Ethyl 2-[6-{1-[(1,1-dimethylethyl)(dimethyl)silyl]-1H-indol-4-yl}-1-(phenylsulfonyl)-1H-indazol-4-yl]-1,3-oxazole-5-carboxylateAusbeute 38,9 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178420574
HCID 178420574, Verbindung
Katalysator
HCID 962WaterLösungsmittel
HCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To a solution of ethyl 2-[6-chloro-1-(phenylsulfonyl)-1H-indazol-4-yl]-1,3-oxazole-5-carboxylate (1.5 g, 3.47 mmol) in 1,4-dioxane (15 ml) and water (1.5 ml) was added {1-[(1,1-dimethylethyl)(dimethyl)silyl]-1H-indol-4-yl}boronic acid (1.243 g, 4.52 mmol, available from Combi-Blocks Inc.), chloro[2′-(dimethylamino)-2-biphenylyl]palladium-1(1R,4S)-bicyclo[2.2.1]hept-2-yl[(1S,4R)-bicyclo[2.2.1]hept-2-yl]phosphane (0.097 g, 0.174 mmol) and potassium phosphate tribasic (2.212 g, 10.42 mmol). The reaction mixture was heated to 100° C. for 3 h, the solvent removed in vacuo and the residue partitioned between dichloromethane (20 ml) and water (10 ml). Saturated sodium chloride solution (100 ml) was added and the organic phase separated and dried over anhydrous sodium sulphate. The crude product was purified by silica gel chromatography, eluting with a gradient of cyclohexane and ethyl acetate. The desired fractions were concentrated to give the title compound as a white solid (0.846 g), which by

Aufarbeitung

  1. customthe solvent removed in vacuo
  2. customthe residue partitioned between dichloromethane (20 ml) and water (10 ml)
  3. additionSaturated sodium chloride solution (100 ml) was added
  4. customthe organic phase separated
  5. dry with materialdried over anhydrous sodium sulphate
  6. customThe crude product was purified by silica gel chromatography
  7. washeluting with a gradient of cyclohexane and ethyl acetate
  8. concentrationThe desired fractions were concentrated

Quellen und Nachweise

ORD-Eintrag
ord-c4889dae5bbb4677b0500c62eaf07667
Quelldatensatz
uspto-grants-2013_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08586590B2

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