Triethylamine → HCID 59305359, Verbindung

HRID 2240968Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2240968
[CH:1]1[CH:6]=[CH:5][C:4]([NH:7][C:8]2[CH:13]=[CH:12][CH:11]=[C:10](Br)[CH:9]=2)=[CH:3][CH:2]=1.[CH:15]([Si:18]([C:25]#[CH:26])([CH:22]([CH3:24])[CH3:23])[CH:19]([CH3:21])[CH3:20])([CH3:17])[CH3:16].C(N(CC)CC)C>[Cu](I)I.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:4]1([NH:7][C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:26]#[C:25][Si:18]([CH:15]([CH3:17])[CH3:16])([CH:22]([CH3:24])[CH3:23])[CH:19]([CH3:21])[CH3:20])[CH:9]=2)[CH:5]=[CH:6][CH:1]=[CH:2][CH:3]=1

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 2734682(Triisopropylsilyl)acetyleneHCID 149586063-Bromodiphenylamine

Produkt 1

HCID 59305359HCID 59305359, VerbindungAusbeute 78 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 83717Copper iodideKatalysatorHCID 178418397HCID 178418397, VerbindungKatalysator

Versuchsvorschrift

Into two Biotage microwave process vials (0.5-2.0 ml) were divided 3-Bromodiphenylamine (636 mg, 2.56 mmol), triisopropylsilylacetylene (0.46 g, 2.56 mmol), copper iodide (20 mg, 0.356 mmol), tetrakis(triphenylphosphine)palladium (60 mg, 0.176 mmol) and triethylamine (3.40 g, 3.36 mmol). The vials were quickly agitated then irradiated in a Biotage Initiator™ microwave instrument for 30 minutes at 80° C. The microwave reactions were recombined and purified by column chromatography (5% EtOAc/hexanes) to afford an oil 698 mg (78%). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.05 (s, 21H) 6.82-6.86 (m, 2H) 7.00-7.12 (m, 4H) 7.15-7.28 (m, 3H) 8.23 (s, 1H); MS (ES) m/z 350.2 [M+H]+

Aufarbeitung

  1. customthen irradiated in a Biotage Initiator™ microwave instrument for 30 minutes at 80° C
  2. custompurified by column chromatography (5% EtOAc/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-c7cae62c8354475abc5139b7d491349e
Quelldatensatz
uspto-grants-2010_05
Patentnummer
US07723368B2

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