Sodium Carbonate → tert-Butyl 2-(3-cyanophenyl)-3-(2'-methylthiobiphenyl-4-ylaminocarbonyl)-3-propylcarbazate

HRID 22641

Reaktionsgleichung

Reaktionsgleichung von HRID 22641
[C:1]([C:3]1[CH:4]=[C:5]([N:9]([N:17]([C:21]([NH:23][C:24]2[CH:29]=[CH:28][C:27](I)=[CH:26][CH:25]=2)=[O:22])[CH2:18][CH2:19][CH3:20])[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH:6]=[CH:7][CH:8]=1)#[N:2].[CH3:31][S:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=1B(O)O.C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[C:1]([C:3]1[CH:4]=[C:5]([N:9]([N:17]([C:21]([NH:23][C:24]2[CH:29]=[CH:28][C:27]([C:34]3[CH:35]=[CH:36][CH:37]=[CH:38][C:33]=3[S:32][CH3:31])=[CH:26][CH:25]=2)=[O:22])[CH2:18][CH2:19][CH3:20])[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH:6]=[CH:7][CH:8]=1)#[N:2]

Komponenten

6

Edukt 3

HCID 10340Sodium CarbonateHCID 27735432-(Methylthio)benzeneboronic acidHCID 11191609tert-Butyl 2-(3-cyanophenyl)-3-(4-iodophenylaminocarbonyl)-3-propylcarbazate

Produkt 1

HCID 22591496tert-Butyl 2-(3-cyanophenyl)-3-(2'-methylthiobiphenyl-4-ylaminocarbonyl)-3-propylcarbazateAusbeute 85,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)KatalysatorHCID 80711,2-DimethoxyethaneLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

1.5 g (2.883 mmol) of 405 and 0.968 g (5.766 mmol) of 2-(methylthio)-phenylboronic acid are dissolved in 100 ml of ethylene glycol dimethyl ether, treated with 63 mg (0.086 mmol) of PdCl2(dppf) and 20.0 ml of 2N sodium carbonate solution and then stirred at 110° C. under a nitrogen atmosphere for 3 h. After customary work-up, 1.28 g (75.9%) of 409 are thus obtained as crystals having a melting point of 184-185° C.; MS(FAB)=517.

Quellen und Nachweise

ORD-Eintrag
ord-2afadabeeba04b919f5703d1f49b9196
Quelldatensatz
uspto-grants-2005_02
Patentnummer
US06849626B2

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