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

Tetrahydrofuran → HCID 11689561, Verbindung

HRID 506275
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 506275
[C:1]([Mg]Br)#[C:2][CH3:3].C1COCC1.[N:11]12[CH2:18][CH2:17][CH:14]([CH2:15][CH2:16]1)[CH:13]([NH:19][C:20]([C:22]1[CH:23]=[CH:24][CH:25]=[C:26]3[O:30][C:29]([C:31]4[CH:36]=[CH:35][C:34](I)=[CH:33][CH:32]=4)=[N:28][C:27]=13)=[O:21])[CH2:12]2>CN(C=O)C.[Cl-].[Zn+2].[Cl-].Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[N:11]12[CH2:18][CH2:17][CH:14]([CH2:15][CH2:16]1)[CH:13]([NH:19][C:20]([C:22]1[CH:23]=[CH:24][CH:25]=[C:26]3[O:30][C:29]([C:31]4[CH:36]=[CH:35][C:34]([C:1]#[C:2][CH3:3])=[CH:33][CH:32]=4)=[N:28][C:27]=13)=[O:21])[CH2:12]2
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 3

HCID 8028TetrahydrofuranHCID 11518485HCID 11518485, VerbindungHCID 178419101HCID 178419101, Verbindung

Produkt 1

HCID 11689561HCID 11689561, VerbindungAusbeute 88 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 3007855ZincchlorideKatalysator
HCID 178418476
HCID 178418476, Verbindung
Katalysator
HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Zinc chloride (1.0 M in ether, 0.33 mL, 0.33 mmol) was added dropwise to a solution of 1-propynylmagnesium bromide in THF (0.5 M in THF, 0.66 mL, 0.33 mmol) at room temperature and the mixture was stirred under nitrogen for 10 min. N-(1-Azabicyclo[2.2.2]oct-3-yl)-2-(4-iodophenyl)benzoxazole-4-carboxamide (50 mg, 0.11 mmol) in DMF (2 mL) was added followed by bis(triphenylphosphine)dichloropalladium(II) (7.7 mg, 0.011 mmol). The resulting mixture was stirred under nitrogen at room temperature for 2 h, and then was quenched with saturated ammonium chloride, extracted with methylene chloride. The combined organic layers were washed with water and brine, dried (Na2SO4), filtered and concentrated. The crude material was purified by column chromatography (silica gel, 90:10:1 ethyl acetate/methanol/concentrated ammonium hydroxide) to afford N-(1-azabicyclo[2.2.2]oct-3-yl)-2-(4-propyn-1-ylphenyl)benzoxazole-4-carboxamide (36 mg, 88%) as a light yellow solid: 1H NMR (300 MHz, CDCl3) δ 9.56 (d, J=7.0 Hz, 1H), 8.23 (dd, J=8.0, 1.0 Hz, 1H), 8.17 (d, J=8.4 Hz, 2H), 7.73 (dd, J=8.0, 1.0 Hz, 1H), 7.58 (d, J=8.4 Hz, 2H), 7.49 (t, J=8.0 Hz, 1H), 4.35-4.29 (m, 1H), 3.54 (ddd, J=14.0, 9.5, 2.0 Hz, 1H), 3.16-2.82 (m, 5H), 2.20-2.03 (m, 2H), 2.14 (s, 3H), 1.80-1.60 (m, 3H); MS (ESI+) m/z 386 (M+H); HPLC>99% (AUC), tR=13.24 min.

Aufarbeitung

  1. stirringThe resulting mixture was stirred under nitrogen at room temperature for 2 h
  2. customwas quenched with saturated ammonium chloride
  3. extractionextracted with methylene chloride
  4. washThe combined organic layers were washed with water and brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude material was purified by column chromatography (silica gel, 90:10:1 ethyl acetate/methanol/concentrated ammonium hydroxide)

Quellen und Nachweise

ORD-Eintrag
ord-bedb136e2357486986809233a2ff0ddc
Quelldatensatz
uspto-grants-2010_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07781430B2

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion