Potassium Carbonate → 3-[1-(ethylsulfonyl)-4-piperidinyl]-5-[4-(4-methyl-2-oxo-1-piperazinyl)phenyl]-1H-indole-7-carboxamide

HRID 562303Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 562303
Br[C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([C:11]([NH2:13])=[O:12])[CH:10]=1)[NH:7][CH:6]=[C:5]2[CH:14]1[CH2:19][CH2:18][N:17]([S:20]([CH2:23][CH3:24])(=[O:22])=[O:21])[CH2:16][CH2:15]1.[CH3:25][N:26]1[CH2:31][CH2:30][N:29]([C:32]2[CH:37]=[CH:36][C:35](B3OC(C)(C)C(C)(C)O3)=[CH:34][CH:33]=2)[C:28](=[O:47])[CH2:27]1.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.O.Cl[Pd-](P(C1CC2CC1CC2)C1CC2CC1CC2)[C-]1C=CC=C1CN(C)C.[CH-]1C=CC=C1.[Fe+2]>[CH2:23]([S:20]([N:17]1[CH2:18][CH2:19][CH:14]([C:5]2[C:4]3[C:8](=[C:9]([C:11]([NH2:13])=[O:12])[CH:10]=[C:2]([C:35]4[CH:34]=[CH:33][C:32]([N:29]5[CH2:30][CH2:31][N:26]([CH3:25])[CH2:27][C:28]5=[O:47])=[CH:37][CH:36]=4)[CH:3]=3)[NH:7][CH:6]=2)[CH2:15][CH2:16]1)(=[O:22])=[O:21])[CH3:24]

Komponenten

7

Edukt 3

HCID 11430Potassium CarbonateHCID 113844275-bromo-3-[1-(ethanesulfonyl)-4-piperidinyl]-1H-indole-7-carboxamideHCID 667228024-Methyl-1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)piperazin-2-one

Produkt 1

HCID 577326733-[1-(ethylsulfonyl)-4-piperidinyl]-5-[4-(4-methyl-2-oxo-1-piperazinyl)phenyl]-1H-indole-7-carboxamideAusbeute 8 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178483166HCID 178483166, VerbindungKatalysatorHCID 962WaterLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
160 °C

Versuchsvorschrift

To 5-bromo-3-[1-(ethylsulfonyl)-4-piperidinyl]-1H-indole-7-carboxamide (20 mg, 0.048 mmol) was added 4-methyl-1-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-2-piperazinone (31 mg, 0.097 mmol) in dioxane (3.0 mL) and H2O (1.0 mL), potassium carbonate (13 mg, 0.097 mmol) and chloro(di-2-norbornylphosphino)(2-dimethylaminomethylferrocen-1-yl)palladium (II) (10 mg, 0.016 mmol). The reaction mixture was reacted in a microwave at 160° C. for 10 min. The reaction mixture was heated in a microwave at 160° C. for 10 min. The reaction mixture was concentrated under Nitrogen and purified by Gilson Preparatory HPLC. The desired fraction in CH3CN and H2O was treated with saturated potassium carbonate to neutralize salts and then concentrated to give 1.9 mg the title compound (8%).

Aufarbeitung

  1. customThe reaction mixture was reacted in a microwave at 160° C. for 10 min
  2. concentrationThe reaction mixture was concentrated under Nitrogen
  3. custompurified by Gilson Preparatory HPLC
  4. additionThe desired fraction in CH3CN and H2O was treated with saturated potassium carbonate
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-07f3bb09e4c04ee887678959d0346212
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08063071B2

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