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Phenylacetylene → HCID 58387189, Verbindung

HRID 1045111
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1045111
[Cl:1][C:2]1[C:3](I)=[CH:4][C:5]2[N:9]=[C:8]([S:10]([CH3:13])(=[O:12])=[O:11])[N:7]([CH2:14][O:15][CH2:16][CH2:17][Si:18]([CH3:21])([CH3:20])[CH3:19])[C:6]=2[CH:22]=1.[C:24]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)#[CH:25].CCOC(C)=O.CO>CN(C=O)C.[Cu](I)I.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>[Cl:1][C:2]1[C:3]([C:25]#[C:24][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[CH:4][C:5]2[N:9]=[C:8]([S:10]([CH3:13])(=[O:12])=[O:11])[N:7]([CH2:14][O:15][CH2:16][CH2:17][Si:18]([CH3:21])([CH3:20])[CH3:19])[C:6]=2[CH:22]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 3

HCID 10821PhenylacetyleneHCID 21584119Ethylacetate methanolHCID 59267806HCID 59267806, Verbindung2×

Produkt 1

HCID 58387189HCID 58387189, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 83717Copper iodideKatalysator
HCID 178418476
HCID 178418476, Verbindung
Katalysator
HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

A 4 mL vial equipped with a stirring bar was charged with copper iodide (2.0 mg, 10 mol %), and Pd(PPh3)2Cl2 (3.5 mg, 5 mol %). A solution of 6-chloro-5-iodo-2-methanesulfonyl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-benzoimidazole (Intermediate 5, 49.0 mg, 0.100 mmol) in DMF (0.5 mL) was added to the vial, followed by a solution of ethynyl-benzene (20.0 mg, 0.200 mmol) in DMF (0.5 mL) and TEA (98 uL, 0.70 mmol). The resulting suspension was stirred at rt for 10 min, during which time it gradually turned brown. The solvent was then removed in vacuo to give brown oily solid, which was suspended in 1:1 EtOAc/MeOH (3 mL) and passed through a Thiol StratoSphere™ SPE cartridge (Polymer Labs). The resulting solution was evaporated to dryness in vacuo to give light yellow oil. LR-MS (API-ES): calculated C22H25ClN2O3SSi 460.1, m/e (M+H)+ not observed, 433.0, 403 (Rt 3.83 min).

Aufarbeitung

  1. customA 4 mL vial equipped with a stirring bar
  2. customThe solvent was then removed in vacuo
  3. customto give brown oily solid, which
  4. customThe resulting solution was evaporated to dryness in vacuo
  5. customto give light yellow oil

Quellen und Nachweise

ORD-Eintrag
ord-62dbfb4403b744349bdafda000f8a832
Quelldatensatz
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08563746B2

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