Reaktion #68561

Reaktionsgleichung

4-((6-chloro-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)methoxy)-7-methoxyquinoline

(3-chloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)methanol

sodium carbonate

→

(2-chloro-4-(3-((7-methoxyquinolin-4-yloxy)methyl)-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)phenyl)methanol

Lösungsmittel

DME

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigewas sparged with argon for 10 min
2. 2
   SonstigeReaction
3. 3
   Sonstigethen partitioned between 9:1 CHCl3/IPA (25 mL) and 5% NaHCO3 (10 mL)
4. 4
   Extraktionaqueous further extracted with 9:1 CHCl3/IPA (2×10 mL)
5. 5
   TrocknenCombined organics dried with MgSO4
6. 6
   Einengenthen concentrated onto dry silica under reduced pressure
7. 7
   SonstigeProduct purified on 40 g silica eluting with 0>12% of 2M NH3 in MeOH/DCM
8. 8
   Sonstigeisolated as an off white powder

Vorschrift

A suspension of 4-((6-chloro-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)methoxy)-7-methoxyquinoline (200 mg, 585 μmol), (3-chloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)methanol (173 mg, 644 μmol), dichloro[1,1′bis(diphenylphoshino)ferrocene]palladium(ii)dichloromethane adduct (21 mg, 29 μmol), and sodium carbonate (2M; 1170 μl, 2341 μmol) in DME (2 mL) was sparged with argon for 10 min then heated to 85° C. for 6 h. Reaction then partitioned between 9:1 CHCl3/IPA (25 mL) and 5% NaHCO3 (10 mL) and aqueous further extracted with 9:1 CHCl3/IPA (2×10 mL). Combined organics dried with MgSO4 then concentrated onto dry silica under reduced pressure. Product purified on 40 g silica eluting with 0>12% of 2M NH3 in MeOH/DCM and isolated as an off white powder. MS (ESI pos. ion) m/z: 448 (MH+). Calc'd exact mass for C23H18ClN5O3: 447.

Quelle