Potassium Carbonate → 5-(5-chloro-2-thienyl)-3-(1-{[3-(1-pyrrolidinyl)propyl]sulfonyl}-4-piperidinyl)-1H-indole-7-carboxamide

HRID 2267529Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2267529
N1([CH2:6][CH2:7][S:8]([N:11]2[CH2:16][CH2:15][CH:14]([C:17]3[C:25]4[C:20](=[C:21]([C:31]([NH2:33])=[O:32])[CH:22]=[C:23](C5C=CSC=5)[CH:24]=4)[NH:19][CH:18]=3)[CH2:13][CH2:12]2)(=[O:10])=[O:9])CCCC1.[Cl:34][C:35]1[S:39][C:38](B(O)O)=[CH:37][CH:36]=1.C(=O)([O-])[O-].[K+].[K+].O1[CH2:54][CH2:53]OCC1>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>[Cl:34][C:35]1[S:39][C:38]([C:23]2[CH:24]=[C:25]3[C:20](=[C:21]([C:31]([NH2:33])=[O:32])[CH:22]=2)[NH:19][CH:18]=[C:17]3[CH:14]2[CH2:13][CH2:12][N:11]([S:8]([CH2:7][CH2:6][CH2:16][N:11]3[CH2:54][CH2:53][CH2:13][CH2:12]3)(=[O:10])=[O:9])[CH2:16][CH2:15]2)=[CH:37][CH:36]=1

Komponenten

7

Edukt 4

HCID 11430Potassium CarbonateHCID 312751,4-Dioxane2×HCID 27343245-Chlorothiophene-2-boronic acidHCID 116200533-(1-{[2-(1-pyrrolidinyl)ethyl]sulfonyl}-4-piperidinyl)-5-(3-thienyl)-1H-indole-7-carboxamide

Produkt 1

HCID 115047545-(5-chloro-2-thienyl)-3-(1-{[3-(1-pyrrolidinyl)propyl]sulfonyl}-4-piperidinyl)-1H-indole-7-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 962WaterLösungsmittel2×

Versuchsvorschrift

The title compound was prepared following the general procedure described in intermediate 16. Thus, 15-bromo-3-(1-{[3-(1-pyrrolidinyl)propyl]sulfonyl}-4-piperidinyl)-1H-indole-7-carboxamide (95 mg, 0.19 mmol) in dioxane (3 mL) and water (1 mL), 5-chloro-2-thienylboronic acid (123 mg, 0.76 mmol), Pd(PPh3)4 (22.2 mg, 10%) and potassium carbonate (211 mg, 1.52 mmol) in dioxane (3.0 mL) and water (1.0 mL) were reacted to form the desired product which was purified by reverse phase HPLC eluting with 10% B to 80% B, where A=H2O (0.1% trifluoroacetic acid) and B=CH3CN (0.1% trifluoroacetic acid) to give the title compound (11 mg, 11%).

Aufarbeitung

  1. customThe title compound was prepared

Quellen und Nachweise

ORD-Eintrag
ord-8d29cd79ba3c4f86a1efb03bb449f4bd
Quelldatensatz
uspto-grants-2010_12
Patentnummer
US07858796B2

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