Reaktion #957805

Reaktionsgleichung

3-bromo-N-(2-methoxyethyl)imidazo[1,2-b]pyridazin-6-amine

(4-(aminomethyl)phenyl)boronic acid

potassium phosphate

→

3-(4-(aminomethyl)phenyl)-N-(2-methoxyethyl)imidazo[1,2-b]pyridazin-6-amine mono acetic acid salt

Lösungsmittel

Dimethoxyethane water

Reaktionsbedingungen

Aufarbeitung

1. 1
   FiltrationThe reaction was then filtered
2. 2
   workup.ADDITIONdiluted with a mixture of 1:1:1 methanol/water/acetonitrile
3. 3
   Filtrationfiltered again
4. 4
   FiltrationThe filtration
5. 5
   Sonstigewas finally purified by preparative HPLC (acidic)

Vorschrift

To a mixture of 3-bromo-N-(2-methoxyethyl)imidazo[1,2-b]pyridazin-6-amine (229 mg, 0.85 mmol), (4-(aminomethyl)phenyl)boronic acid (395 mg, 2.11 mmol), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (62 mg, 0.085 mmol) and potassium phosphate (540 mg, 2.54 mmol) was added 1:1 Dimethoxyethane/water (3 mL). The resulting mixture was heated at 160° C. (microwave) for 6 min. The reaction was then filtered and diluted with a mixture of 1:1:1 methanol/water/acetonitrile, and then filtered again. The filtration was finally purified by preparative HPLC (acidic) to afford 3-(4-(aminomethyl)phenyl)-N-(2-methoxyethyl)imidazo[1,2-b]pyridazin-6-amine mono acetic acid salt as a white solid: 1H NMR (METHANOL-d4) δ: 8.18-8.33 (m, J=8.3 Hz, 2H), 7.82 (s, 1H), 7.67 (d, J=9.6 Hz, 1H), 7.53-7.58 (m, J=8.3 Hz, 2H), 6.78 (d, J=9.6 Hz, 1H), 4.14 (s, 2H), 3.68 (t, J=5.7 Hz, 2H), 3.58 (t, J=5.4 Hz, 2H), 3.42 (s, 3H), 1.93 (s, 3H); LRMS (ESI) m/e 298.2 [(M+H)+, calcd for C16H20N5O 298.2]

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