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Potassium Carbonate → 3-[(1,1-Dioxidotetrahydro-3-thienyl)methyl]-5-phenyl-1H-indole-7-carboxamide

HRID 387398
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 387398
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[CH2:14][CH:15]1[CH2:19][CH2:18][S:17](=[O:21])(=[O:20])[CH2:16]1.[C:22]1(B(O)O)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.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]>[O:20]=[S:17]1(=[O:21])[CH2:18][CH2:19][CH:15]([CH2:14][C:5]2[C:4]3[C:8](=[C:9]([C:11]([NH2:13])=[O:12])[CH:10]=[C:2]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)[CH:3]=3)[NH:7][CH:6]=2)[CH2:16]1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 3

HCID 11430Potassium CarbonateHCID 66827Phenylboronic AcidHCID 593326215-Bromo-3-[(1,1-dioxidotetrahydro-3-thienyl)methyl]-1H-indole-7-carboxamide

Produkt 1

HCID 593326393-[(1,1-Dioxidotetrahydro-3-thienyl)methyl]-5-phenyl-1H-indole-7-carboxamideAusbeute 88,7 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 44119782
Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)
Katalysator
HCID 962WaterLösungsmittel
HCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

5-bromo-3-[(1,1-dioxidotetrahydro-3-thienyl)methyl]-1H-indole-7-carboxamide (40 mg, 0.108 mmol), phenylboronic acid (19.71 mg, 0.162 mmol, 1.5 eq), PdCl2(dppf) (7.88 mg, 10.77 μmol, 0.1 eq), potassium carbonate (44.7 mg, 0.323 mmol, 3 eq) were diluted in a mixture of 1,4-dioxane (3 mL) and water (1 mL), in a 2-5 mL biotage microwave reaction tube. The mixture was degassed by bubbling nitrogen through for 5 minutes and was then heated in a microwave at high absorption for 15 minutes at 120° C. The reaction was filtered through a thiol SPE cartridge (polymer labs) and was concentrated and purified by Gilson HPLC with trifluoroacetic acid buffer. The desired product fractions were combined and concentrated in an EZ2 Genevac evaporator, giving 35.3 mg (84%) of the title compound.

Aufarbeitung

  1. customThe mixture was degassed
  2. customby bubbling nitrogen through for 5 minutes
  3. filtrationThe reaction was filtered through a thiol SPE cartridge (polymer labs)
  4. concentrationwas concentrated
  5. custompurified by Gilson HPLC with trifluoroacetic acid buffer
  6. concentrationconcentrated in an EZ2 Genevac evaporator

Quellen und Nachweise

ORD-Eintrag
ord-99946cedd00a4bf1a1aa9d3e0f8ddb6d
Quelldatensatz
uspto-grants-2013_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08372875B2

Notizen zur Reaktion

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