Sodium Carbonate → 5-(2-aminopyrimidin-4-yl)-2-(2-chloro-5-cyanophenyl)-1H-pyrrole-3-carboxamide

HRID 924682Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 924682
[NH2:1][C:2]1[N:7]=[C:6]([C:8]2[NH:12][C:11](Br)=[C:10]([C:14]([NH2:16])=[O:15])[CH:9]=2)[CH:5]=[CH:4][N:3]=1.[Cl:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]#[N:25])=[CH:20][C:19]=1B(O)O.C([O-])([O-])=O.[Na+].[Na+]>COCCOC.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]>[NH2:1][C:2]1[N:7]=[C:6]([C:8]2[NH:12][C:11]([C:19]3[CH:20]=[C:21]([C:24]#[N:25])[CH:22]=[CH:23][C:18]=3[Cl:17])=[C:10]([C:14]([NH2:16])=[O:15])[CH:9]=2)[CH:5]=[CH:4][N:3]=1

Komponenten

7

Edukt 3

HCID 10340Sodium CarbonateHCID 27632792-Chloro-5-cyanophenylboronic acidHCID 497882145-(2-aminopyrimidin-4-yl)-2-bromo-1H-pyrrole-3-carboxamide

Produkt 1

HCID 665710105-(2-aminopyrimidin-4-yl)-2-(2-chloro-5-cyanophenyl)-1H-pyrrole-3-carboxamideAusbeute 13 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)KatalysatorHCID 962WaterLösungsmittelHCID 80711,2-DimethoxyethaneLösungsmittel

Versuchsvorschrift

5-(2-Aminopyrimidin-4-yl)-2-bromo-1H-pyrrole-3-carboxamide (prepared according to WO2007/110344, 0.1 g, 0.35 mmol), 2-chloro-5-cyanophenylboronic acid (127 mg, 0.7 mmol), Na2CO3 (111 mg, 1.05 mmol), and PdCl2(dppf) (28 mg, 0.035 mmol) in DME (2.5 mL) and water (1 mL) were heated at 80° C. for 12 h, under argon. After cooling to room temperature, the precipitate was filtered and the filtrate was evaporated under reduced pressure. The crude material was purified by preparative HPLC (Method 1) to afford the title compound (15 mg, 13%).

Aufarbeitung

  1. filtrationthe precipitate was filtered
  2. customthe filtrate was evaporated under reduced pressure
  3. customThe crude material was purified by preparative HPLC (Method 1)

Quellen und Nachweise

ORD-Eintrag
ord-008ae75dd38741b5b8cd37fd04c35427
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09283224B2

Notizen zur Reaktion

Wird geladen…