Sodium Carbonate → 1-tert-butyl 2-methyl 4-[4-(4-aminophenoxy)pyridin-2-yl]-1H-pyrrole-1,2-dicarboxylate

HRID 1402523Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1402523
Cl[C:2]1[CH:7]=[C:6]([O:8][C:9]2[CH:15]=[CH:14][C:12]([NH2:13])=[CH:11][CH:10]=2)[CH:5]=[CH:4][N:3]=1.CC1(C)C(C)(C)OB([C:24]2[CH:25]=[C:26]([C:36]([O:38][CH3:39])=[O:37])[N:27]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH:28]=2)O1.C([O-])([O-])=O.[Na+].[Na+].O1CCOCC1>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.O>[NH2:13][C:12]1[CH:14]=[CH:15][C:9]([O:8][C:6]2[CH:5]=[CH:4][N:3]=[C:2]([C:24]3[CH:25]=[C:26]([C:36]([O:38][CH3:39])=[O:37])[N:27]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH:28]=3)[CH:7]=2)=[CH:10][CH:11]=1

Komponenten

7

Edukt 4

HCID 10340Sodium CarbonateHCID 312751,4-DioxaneHCID 445577501-tert-butyl 2-methyl 4-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrole-1,2-dicarboxylateHCID 578334304-(2-Chloro-pyridin-4-yloxy)-phenylamine

Produkt 1

HCID 581679381-tert-butyl 2-methyl 4-[4-(4-aminophenoxy)pyridin-2-yl]-1H-pyrrole-1,2-dicarboxylate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418476HCID 178418476, VerbindungKatalysatorHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

A 100 ml flask was charged with 4-((2-chloropyridin-4-yl)oxy)aniline (150 mg, 0.68 mmol), 1-tert-butyl 2-methyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrole-1,2-dicarboxylate (260 mg, 0.81 mmol), 2M Na2CO3 solution (0.5 ml, 1.0 mmol), PdCl2(PPh3)2 (5 mg, 0.007 mmol), 10 ml of 1,4-dioxane and 3 ml of water. The mixture was flushed with nitrogen and heated at 70° C. for 30 minutes. The mixture was cooled to room temperature and poured into 100 ml of water. The precipitates were filtered and dried to give the crude, which was further purified by silica gel chromatography eluting with 2-3% MeOH/CHCl3 to give 1-tert-butyl 2-methyl 4-[4-(4-aminophenoxy)pyridin-2-yl]-1H-pyrrole-1,2-dicarboxylate as light brown oil.

Aufarbeitung

  1. customThe mixture was flushed with nitrogen
  2. temperatureThe mixture was cooled to room temperature
  3. additionpoured into 100 ml of water
  4. filtrationThe precipitates were filtered
  5. customdried
  6. customto give the crude, which
  7. customwas further purified by silica gel chromatography
  8. washeluting with 2-3% MeOH/CHCl3

Quellen und Nachweise

ORD-Eintrag
ord-0589872aeab34d4fa0b01ec805cfa0fb
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08906944B2

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