Potassium Carbonate → 5-[5-(1-Azetidinylmethyl)-3-thienyl]-3-(1,1-dioxidotetrahydro-3-thienyl)-1H-indole-7-carboxamide

HRID 656121Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 656121
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[CH2:18][CH2:17][S:16](=[O:20])(=[O:19])[CH2:15]1.CC1(C)C(C)(C)OB([C:29]2[CH:30]=[C:31]([CH2:34][N:35]3[CH2:38][CH2:37][CH2:36]3)[S:32][CH:33]=2)O1.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.O.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]>[N:35]1([CH2:34][C:31]2[S:32][CH:33]=[C:29]([C:2]3[CH:3]=[C:4]4[C:8](=[C:9]([C:11]([NH2:13])=[O:12])[CH:10]=3)[NH:7][CH:6]=[C:5]4[CH:14]3[CH2:18][CH2:17][S:16](=[O:20])(=[O:19])[CH2:15]3)[CH:30]=2)[CH2:38][CH2:37][CH2:36]1

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 593325635-bromo-3-(1,1-dioxidotetrahydro-3-thienyl)-1H-indole-7-carboxamideHCID 593327081-{[4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-2-thienyl]methyl}azetidine

Produkt 1

HCID 250722255-[5-(1-Azetidinylmethyl)-3-thienyl]-3-(1,1-dioxidotetrahydro-3-thienyl)-1H-indole-7-carboxamideAusbeute 23 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)KatalysatorHCID 218864351,4-Dioxane--water (1/1)Lösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

5-bromo-3-(1,1-dioxidotetrahydro-3-thienyl)-1H-indole-7-carboxamide (0.040 g, 0.112 mmol) and 1-{[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-thienyl]methyl}azetidine (0.035 g, 0.126 mmol, 1.1 eq) was dissolved in a 6:1 solution of 1,4 dioxane/water in a 20 mL microwave reaction vessel. Potassium carbonate (0.077 g, 0.560 mmol, 5 eq) was added and the solution was degassed with Argon. PdCl2(dppf) (0.014 g, 0.019 mmol) was added and the reaction was heated in a microwave at 100° C. for 20 min. Solution was passed through a StratoSphere SPE PL-Thiol MP SPE column to remove palladium and purified on Gilson preparative HPLC using Acetonitrile/Water with 0.1% TFA. The desired fractions were concentrated, giving 0.011 g (23%) of the title compound.

Aufarbeitung

  1. customthe solution was degassed with Argon
  2. customto remove palladium
  3. custompurified on Gilson preparative HPLC
  4. concentrationThe desired fractions were concentrated

Quellen und Nachweise

ORD-Eintrag
ord-d443c18e4e47419ca6d2618ccf948d6e
Quelldatensatz
uspto-grants-2011_12
Patentnummer
US08071584B2

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