StartseiteMCPWorkbenchSkills
StartseiteWorkbenchBenachrichtigungenMein Bereich
llms.txt · MCP-AnleitungDatenschutz · Nutzungsbedingungen · Supportv1.8.0
  1. Startseite
  2. /Reaktion

Potassium Carbonate → 4,6-difluoro-5-[4-(1-hydroxy-2-methylpropan-2-yl)phenyl]-1H-indole-3-carbaldehyde

HRID 1054635
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1054635
CC1(C)COB([C:8]2[CH:13]=[CH:12][C:11]([C:14]([CH3:18])([CH3:17])[CH2:15][OH:16])=[CH:10][CH:9]=2)OC1.Br[C:21]1[C:22]([F:33])=[C:23]2[C:27](=[CH:28][C:29]=1[F:30])[NH:26][CH:25]=[C:24]2[CH:31]=[O:32].C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1.CCO.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]>[F:33][C:22]1[C:21]([C:8]2[CH:9]=[CH:10][C:11]([C:14]([CH3:17])([CH3:18])[CH2:15][OH:16])=[CH:12][CH:13]=2)=[C:29]([F:30])[CH:28]=[C:27]2[C:23]=1[C:24]([CH:31]=[O:32])=[CH:25][NH:26]2
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 3

HCID 11430Potassium CarbonateHCID 866985785-Bromo-4,6-difluoro-1H-indole-3-carbaldehydeHCID 866986392-(4-(5,5-Dimethyl-1,3,2-dioxaborinan-2-yl)phenyl)-2-methylpropan-1-ol

Produkt 1

HCID 866986404,6-difluoro-5-[4-(1-hydroxy-2-methylpropan-2-yl)phenyl]-1H-indole-3-carbaldehydeAusbeute 32 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 44119782
Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)
Katalysator
HCID 702EthanolLösungsmittel
HCID 962WaterLösungsmittel
HCID 1140TolueneLösungsmittel

Versuchsvorschrift

To a solution of 2-[4-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)phenyl]-2-methylpropan-1-ol (102 mg, 0.386 mmol) and 5-bromo-4,6-difluoro-1H-indole-3-carbaldehyde (100 mg, 0.386 mmol) in toluene (6 mL) and EtOH (2 mL) was added a solution of potassium carbonate (160 mg, 1.159 mmol) in water (1.0 mL) and Pd(dppf)Cl2 (15.8 mg, 0.019 mmol) at room temperature under N2. The reaction was cooled to room temperature, and extracted with ethyl acetate (10 mL×2). The organic layers were washed with brine (10 mL), and dried over sodium sulfate and concentrated to give a crude residue, which was purified by column chromatography to give the title compound (40 mg, 32%) as a yellow solid. 1H NMR (400 MHz, CD3OD) δ 10.0 (s, 1 H), 8.13 (s, 1 H), 7.51 (d, 2 H), 7.40 (d, 2 H), 7.19 (d, 1 H), 3.63 (s, 2 H), 1.36 (s, 6 H).

Aufarbeitung

  1. extractionextracted with ethyl acetate (10 mL×2)
  2. washThe organic layers were washed with brine (10 mL)
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. customto give a crude residue, which
  6. customwas purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-75cd2b174edc49e4baa40e7cd6f64bef
Quelldatensatz
uspto-grants-2016_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09394285B2

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion