Dimethyl Sulfoxide → 7-Methoxy-4-((6-phenylimidazo[1,2-b]pyridazin-3-yl)methoxy)quinoline

HRID 219117Notes

Reaction equation

HRID 219117 reaction equation
[C:1]1([C:7]2[CH:8]=[CH:9][C:10]3[N:11]([C:13]([CH2:16][OH:17])=[CH:14][N:15]=3)[N:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl[C:19]1[C:28]2[C:23](=[CH:24][C:25]([O:29][CH3:30])=[CH:26][CH:27]=2)[N:22]=[CH:21][CH:20]=1.C([O-])([O-])=O.[Cs+].[Cs+].CS(C)=O>O>[CH3:30][O:29][C:25]1[CH:24]=[C:23]2[C:28]([C:19]([O:17][CH2:16][C:13]3[N:11]4[N:12]=[C:7]([C:1]5[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=5)[CH:8]=[CH:9][C:10]4=[N:15][CH:14]=3)=[CH:20][CH:21]=[N:22]2)=[CH:27][CH:26]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 10796Cesium carbonateHCID 106078294-Chloro-7-methoxyquinolineHCID 67503278(6-Phenylimidazo[1,2-b]pyridazin-3-yl)methanol

Product 1

HCID 576909607-Methoxy-4-((6-phenylimidazo[1,2-b]pyridazin-3-yl)methoxy)quinoline

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In a microwave vessel, (6-phenylimidazo[1,2-b]pyridazin-3-yl)methanol (0.075 g, 0.33 mmol), 4-chloro-7-methoxyquinoline (0.19 g, 1.00 mmol), Cs2CO3 (0.22 g, 0.67 mmol) and 0.7 mL DMSO were combined and the vessel sealed. The mixture was pre-stirred for 2 min, followed by microwave heating for 2 h at 120 C, then 1 h at 130 C. The mixture was allowed to cool to rt, diluted with water to precipitate a cream solid. The solid was collected and rinsed with water. The solid was purified via flash chromatography using a 0% to 5% MeOH in EtOAc gradient to afford the title compound as a yellow solid. M/Z=383.2 [M+H], calc 382.4212 for C23H18N4O2. The following compounds were prepared using the method described for 7-methoxy-4-((6-phenylimidazo[1,2-b]pyridazin-3-yl)methoxy)quinoline:

Workup

  1. customthe vessel sealed
  2. temperatureheating for 2 h at 120 C
  3. custom1 h
  4. customto precipitate a cream solid
  5. customThe solid was collected
  6. washrinsed with water
  7. customThe solid was purified via flash chromatography

Sources & evidence

ORD record
ord-070820ee2d774550abedc61c7d8cd58a
Source dataset
uspto-grants-2012_06
Patent number
US08198448B2

Reaction notes

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