1,2-Dimethoxyethane → 3-[6-Bromo-8-(2-pyridin-4-yl-imidazol-1-yl)-imidazo[1,2-a]pyrazin-6-yl]-phenylamine

HRID 457672

Reaktionsgleichung

Reaktionsgleichung von HRID 457672
[Br:1][C:2]1[N:3]=[C:4]([N:11]2[CH:15]=[CH:14][N:13]=[C:12]2[C:16]2[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=2)[C:5]2[N:6]([CH:8]=[CH:9][N:10]=2)[CH:7]=1.Cl.[NH2:23][C:24]1[CH:25]=[C:26](B(O)O)[CH:27]=[CH:28][CH:29]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].COCCOC>[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O>[Br:1][C:2]1([C:28]2[CH:29]=[C:24]([NH2:23])[CH:25]=[CH:26][CH:27]=2)[CH2:7][N:6]2[CH:8]=[CH:9][N:10]=[C:5]2[C:4]([N:11]2[CH:15]=[CH:14][N:13]=[C:12]2[C:16]2[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=2)=[N:3]1

Komponenten

7

Edukt 4

HCID 80711,2-DimethoxyethaneHCID 62657Potassium Phosphate, TribasicHCID 27632413-Aminophenylboronic acid hydrochlorideHCID 184403196-Bromo-8-(2-pyridin-4-yl-imidazol-1-yl)-imidazo[1,2-a]pyrazine

Produkt 1

HCID 184403173-[6-Bromo-8-(2-pyridin-4-yl-imidazol-1-yl)-imidazo[1,2-a]pyrazin-6-yl]-phenylamineAusbeute 66 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumKatalysatorHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
95 °C

Versuchsvorschrift

A mixture of 6-bromo-8-(2-pyridin-4-yl-imidazol-1-yl)-imidazo[1,2-a]pyrazine (4) (4.0 g), 3-aminophenylboronic acid hydrochloride (2.41 g), tetrakis(triphenylphosphine) palladium (Pd(PPh3)4) (1.36 g), 2.5 Maqueous potassium phosphate (K3PO3) (10 ml), and 1,2-dimethoxyethane (DME) (80 ml) is heated at 95° C. for 16 hours. The mixture is cooled to rt, treated with water (50 ml) and extracted with ethyl acetate (3×80 ml). The extracts are washed with water (1×50 ml) and brine (1×50 ml), dried over Na2SO4, and evaporated in vacuo. Purification on SiO2 (5% MeOH, DCM) yielded 3-[6 -Bromo-8-(2-pyridin-4-yl-imidazol-1-yl)-imidazo[1,2-a]pyrazin-6-yl]-phenylamine (5) (3.36 g) as a cream solid.

Aufarbeitung

  1. temperatureThe mixture is cooled to rt
  2. extractionextracted with ethyl acetate (3×80 ml)
  3. washThe extracts are washed with water (1×50 ml) and brine (1×50 ml)
  4. dry with materialdried over Na2SO4
  5. customevaporated in vacuo
  6. customPurification on SiO2 (5% MeOH, DCM)

Quellen und Nachweise

ORD-Eintrag
ord-00c6666bd043402199cb6618075b0413
Quelldatensatz
uspto-grants-2007_03
Patentnummer
US07189723B2

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