Water → HCID 178472397, Verbindung

HRID 2095643Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2095643
Br[C:2]1[CH:3]=[C:4]2[C:10]([C@@H:11]([C:13]3[C:18]([O:19][CH3:20])=[CH:17][CH:16]=[C:15]([F:21])[C:14]=3[Cl:22])[CH3:12])=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1.[CH3:23][C:24]1[N:28]([C@H:29]2[CH2:34][CH2:33][C@H:32]([C:35]([O:37][CH2:38][CH3:39])=[O:36])[CH2:31][CH2:30]2)[N:27]=[CH:26][C:25]=1B1OC(C)(C)C(C)(C)O1.[F-].[K+].O>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O1CCOCC1>[Cl:22][C:14]1[C:15]([F:21])=[CH:16][CH:17]=[C:18]([O:19][CH3:20])[C:13]=1[C@H:11]([C:10]1[C:4]2[C:5](=[N:6][CH:7]=[C:2]([C:25]3[CH:26]=[N:27][N:28]([C@H:29]4[CH2:30][CH2:31][C@H:32]([C:35]([O:37][CH2:38][CH3:39])=[O:36])[CH2:33][CH2:34]4)[C:24]=3[CH3:23])[CH:3]=2)[NH:8][CH:9]=1)[CH3:12]

Komponenten

7

Edukt 4

HCID 962WaterHCID 522689Potassium FluorideHCID 670045375-Bromo-3-[(S)-1-(2-chloro-3-fluoro-6-methoxyphenyl)-ethyl]-1H-pyrrolo[2,3-b]pyridineHCID 178472396HCID 178472396, Verbindung

Produkt 1

HCID 178472397HCID 178472397, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

A mixture of 5-bromo-3-[(S)-1-(2-chloro-3-fluoro-6-methoxyphenyl)-ethyl]-1H-pyrrolo[2,3-b]pyridine (57.8 mg, 0.150 mmol), ethyl trans-4-[5-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]cyclohexanecarboxylate (60.0 mg, 0.166 mmol), Pd(PPh3)4 (8.70 mg, 0.00753 mmol), potassium fluoride (26.2 mg, 0.452 mmol) and 4:1 dioxane:H2O (3 mL, 30 mmol) was heated to 90° C. for 2 h. The organic solvent was removed in vacuo, and the material was extracted with DCM and water. The organic layer was purified via column chromatography, eluting with 1-3% MeOH/DCM. The fractions containing the pure product were concentrated in vacuo to afford the title compound as a white solid. MS (ES+): m/z=539.16/541.16 (100/50) [MH+]. HPLC: tR=3.98 min (polar—5 min, ZQ3).

Aufarbeitung

  1. customThe organic solvent was removed in vacuo
  2. extractionthe material was extracted with DCM and water
  3. customThe organic layer was purified via column chromatography
  4. washeluting with 1-3% MeOH/DCM
  5. additionThe fractions containing the pure product
  6. concentrationwere concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-92f3dce6ae464cddbc093bb500252ca9
Quelldatensatz
uspto-grants-2013_05
Patentnummer
US08445510B2

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