Water → HCID 58182165, Verbindung

HRID 2088429

Reaktionsgleichung

Reaktionsgleichung von HRID 2088429
Br[C:2]1[S:3][CH:4]=[C:5]([C:7]([NH:9][C:10]2[CH:11]=[N:12][CH:13]=[CH:14][C:15]=2[N:16]2[CH2:21][CH2:20][CH2:19][C@H:18]([NH:22][C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26])[CH2:17]2)=[O:8])[N:6]=1.[F:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=1B(O)O.C([O-])(=O)C.[K+].O>C(=O)([O-])[O-].[Na+].[Na+].C(#N)C.[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[F:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=1[C:2]1[S:3][CH:4]=[C:5]([C:7]([NH:9][C:10]2[CH:11]=[N:12][CH:13]=[CH:14][C:15]=2[N:16]2[CH2:21][CH2:20][CH2:19][C@H:18]([NH:22][C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26])[CH2:17]2)=[O:8])[N:6]=1

Komponenten

8

Edukt 4

HCID 962Water2×HCID 517044Potassium AcetateHCID 27343542-Fluorophenylboronic acidHCID 58182192(S)-tert-butyl 1-(3-(2-bromothiazole-4-carboxamido)pyridin-4-yl)piperidin-3-ylcarbamate

Produkt 1

HCID 58182165HCID 58182165, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)KatalysatorHCID 6342AcetonitrileLösungsmittelHCID 10340Sodium CarbonateLösungsmittel

Versuchsvorschrift

In a microwave safe sealed tube was charged a mixture of ((S)-tert-butyl 1-(3-(2-bromothiazole-4-carboxamido)pyridin-4-yl)piperidin-3-ylcarbamate (96.5 mg, 0.2 mmol), 2-Fluorophenylboronic acid (33.6 mg, 0.24 mmol), 1,1′-Bis(diphenylphosphino)ferrocene palladium (II) chloride (81.7 mg, 0.1 mmol), 1.00 M of Potassium acetate in Water (0.3 mL, 0.3 mmol), 1.00 M of Sodium carbonate in Water (0.3 mL, 0.3 mmol) in acetonitrile (5 mL). The mixture was irradiated at 300 W 110° C. for 15 minutes. The reaction mixture was then concentrated and the residue was purified on silica eluting with 0 to 5% MeOH in DCM with 1% NH4OH (90.0 mg, 90.4%). ESIMS m/z=498.2 (M+1).

Aufarbeitung

  1. additionIn a microwave safe sealed tube was charged
  2. customThe mixture was irradiated at 300 W 110° C. for 15 minutes
  3. concentrationThe reaction mixture was then concentrated
  4. customthe residue was purified on silica eluting with 0 to 5% MeOH in DCM with 1% NH4OH (90.0 mg, 90.4%)

Quellen und Nachweise

ORD-Eintrag
ord-4b7fb7376b444df6b810df857608bfc7
Quelldatensatz
uspto-grants-2013_05
Patentnummer
US08435976B2

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