Potassium Carbonate → 3-cyclopentyl-1-methyl-2-pyridin-2-yl-1H-indole-6-carboxylic acid methyl ester

HRID 1246270Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1246270
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7](Cl)=[C:6]([NH2:11])[CH:5]=1.[CH:13]1([C:18]#[C:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=2)[CH2:17][CH2:16][CH2:15][CH2:14]1.[C:26]([O-])([O-])=O.[K+].[K+]>CC([O-])=O.CC([O-])=O.[Pd+2].CC(P(C(C)(C)C)C1[CH-]C=CC=1)(C)C.CC(P(C(C)(C)C)C1[CH-]C=CC=1)(C)C.[Fe+2].CN1C(=O)CCC1>[CH3:1][O:2][C:3]([C:4]1[CH:5]=[C:6]2[C:7]([C:18]([CH:13]3[CH2:17][CH2:16][CH2:15][CH2:14]3)=[C:19]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=3)[N:11]2[CH3:26])=[CH:8][CH:9]=1)=[O:12]

Komponenten

7

Edukt 3

HCID 11430Potassium CarbonateHCID 593055Methyl 3-Amino-4-chlorobenzoateHCID 219166132-(Cyclopentylethynyl)pyridine

Produkt 1

HCID 587209163-cyclopentyl-1-methyl-2-pyridin-2-yl-1H-indole-6-carboxylic acid methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 167845palladium(II) acetateKatalysatorHCID 713105441,1'-Bis(di-tert-butylphosphino)ferroceneKatalysatorHCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Reaktionsbedingungen

Temperatur
130 °C

Versuchsvorschrift

A 100 mL three neck flask equipped with a thermocouple, condenser and stir bar was purged with argon. 3-Amino-4-chlorobenzoic acid methyl ester (5.0 g, 26.94 mmol), 2-cyclopentylethynyl-pyridine (5.528 g, 32.33 mmol), Pd(OAc)2 (181 mg, 0.81 mmol), DtBPF (767 mg, 1.62 mmol), K2CO3 (9.29 g, 67.35 mmol) and NMP (25 mL) were then charged. The reaction was heated to 130° C. and monitored by HPLC. The reaction was complete after 6 hours.

Aufarbeitung

  1. customwas purged with argon

Quellen und Nachweise

ORD-Eintrag
ord-d72da3e530c4440cb09ec55945308d67
Quelldatensatz
uspto-grants-2006_10
Patentnummer
US07126009B2

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