Triethylamine → 6-(5-Methoxy-benzofuran-2-yl)-pyridazin-3-ylamine

HRID 501047

Reaktionsgleichung

Reaktionsgleichung von HRID 501047
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[O:10][C:9](B(O)O)=[CH:8][C:7]=2[CH:14]=1.Br[C:16]1[N:21]=[N:20][C:19]([NH2:22])=[CH:18][CH:17]=1.CCN(CC)CC>CCO.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>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[O:10][C:9]([C:16]3[N:21]=[N:20][C:19]([NH2:22])=[CH:18][CH:17]=3)=[CH:8][C:7]=2[CH:14]=1

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 27947796-Bromopyridazin-3-amineHCID 22221596(5-Methoxy-1-benzofuran-2-yl)boronic acid

Produkt 1

HCID 250149286-(5-Methoxy-benzofuran-2-yl)-pyridazin-3-ylamineAusbeute 21,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418476HCID 178418476, VerbindungKatalysatorHCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
140 °C

Versuchsvorschrift

5-methoxybenzofuran boronic acid 1.2 mmol), 6-bromo-3-pyridazinamine (1.0 mmol), Pd(PPh3)2Cl2 (0.024 mmol) and NEt3 (317 μL) were mixed in EtOH (10 mL) in a 20 mL microwave vial. The mixture was stirred at 140° C. for 10 min in a microwave reactor. The solvent was removed under vacuum, water was added and the solution was extracted with EtOAc. The organic layer was dried over Na2SO4, filtered and the solvent removed under vacuum. The crude substance was purified by preparative HPLC to afford the title compound as a white solid (51 mg). 1H NMR δ ppm 7.77 (d, 1 H) 7.52 (d, 1 H) 7.35 (s, 1H) 7.19 (d, 1 H) 6.79-6.98 (m, 2 H) 6.72 (s, 2 H) 3.80 (s, 3 H); MS m/z 242 (M+H).

Aufarbeitung

  1. customThe solvent was removed under vacuum, water
  2. additionwas added
  3. extractionthe solution was extracted with EtOAc
  4. dry with materialThe organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. customthe solvent removed under vacuum
  7. customThe crude substance was purified by preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-e336682ef11347baaef493fc5392dfac
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07772256B2

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