1,2-Dimethoxyethane → 2-Acetylamino-3-cyano-5-(4-cyanophenyl)thiophene

HRID 900446Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 900446
[C:1]([NH:4][C:5]1[S:6][C:7](Br)=[CH:8][C:9]=1[C:10]#[N:11])(=[O:3])[CH3:2].[C:13]([C:15]1[CH:20]=[CH:19][C:18](B(O)O)=[CH:17][CH:16]=1)#[N:14].C(=O)([O-])[O-].[K+].[K+].C(COC)OC>O>[C:1]([NH:4][C:5]1[S:6][C:7]([C:18]2[CH:19]=[CH:20][C:15]([C:13]#[N:14])=[CH:16][CH:17]=2)=[CH:8][C:9]=1[C:10]#[N:11])(=[O:3])[CH3:2]

Komponenten

6

Edukt 4

HCID 80711,2-DimethoxyethaneHCID 11430Potassium CarbonateHCID 27343264-Cyanophenylboronic acidHCID 130528502-Acetylamino-5-bromo-3-cyanothiophene

Produkt 1

HCID 179309842-Acetylamino-3-cyano-5-(4-cyanophenyl)thiopheneAusbeute 86,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

2-Acetylamino-5-bromo-3-cyanothiophene (500 mg), 4-cyanophenylboronic acid (360 mg) and potassium carbonate (845 mg) were added to dimethoxyethane (15 ml) and water (2 ml) and the system purged with argon for 15 minutes. Tetrakis(triphenylphosphine)palladium(0) (236 mg) was added and the mixture heated at 80° C. for 3.25 h. The mixture was cooled, concentrated under reduced pressure to remove most of the dimethoxymethane, dichloromethane added and the mixture filtered to give the product as a pale brown solid (470 mg).

Aufarbeitung

  1. customthe system purged with argon for 15 minutes
  2. additionTetrakis(triphenylphosphine)palladium(0) (236 mg) was added
  3. temperatureThe mixture was cooled
  4. concentrationconcentrated under reduced pressure
  5. customto remove most of the dimethoxymethane, dichloromethane
  6. additionadded
  7. filtrationthe mixture filtered

Quellen und Nachweise

ORD-Eintrag
ord-a2eb6bb84e6e47f0b713b54c043d71be
Quelldatensatz
uspto-grants-2008_04
Patentnummer
US07358376B2

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