Cesium carbonate → 6-[6-(3,4-Difluoro-phenoxy)-[1,2,4]triazolo[4,3-b]pyridazin-3-ylmethyl]-quinoline

HRID 655279Notes

Reaction equation

HRID 655279 reaction equation
Cl[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([CH2:11][C:12]3[CH:13]=[C:14]4[C:19](=[CH:20][CH:21]=3)[N:18]=[CH:17][CH:16]=[CH:15]4)=[N:9][N:10]=2)[N:7]=1.[F:22][C:23]1[CH:24]=[C:25]([OH:30])[CH:26]=[CH:27][C:28]=1[F:29].C([O-])([O-])=O.[Cs+].[Cs+]>CS(C)=O>[F:22][C:23]1[CH:24]=[C:25]([CH:26]=[CH:27][C:28]=1[F:29])[O:30][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([CH2:11][C:12]3[CH:13]=[C:14]4[C:19](=[CH:20][CH:21]=3)[N:18]=[CH:17][CH:16]=[CH:15]4)=[N:9][N:10]=2)[N:7]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 759273,4-DifluorophenolHCID 249683676-((6-Chloro-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)methyl)quinoline

Product 1

HCID 593202786-[6-(3,4-Difluoro-phenoxy)-[1,2,4]triazolo[4,3-b]pyridazin-3-ylmethyl]-quinolineYield 34.5%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of 6-(6-chloro-[1,2,4]triazolo[4,3-b]pyridazin-3-ylmethyl)-quinoline (60 mg, 0.203 mmol, 1.0 equiv.), 3,4-difluorophenol (0.223 mmol, 1.1 equiv.), Cs2CO3 (86 mg, 0.264 mmol, 1.3 equiv) and dimethylsulfoxide (1 mL) were mixed in a microwave tube and capped. The microwave tube was reacted in a microwave reactor (Personel Chemistry, Emrys Optimizer) at 70° C. for 10 minutes. The solvent was removed by rotary evaporation and the crude product purified via flash column chromatography (SiO2, CH2Cl2:CH3OH 100:0-80:20) to return the title compound as a white solid (27.2 mg, 0.07 mmol, 34% yield). Analytical data presented in Table 1.

Workup

  1. customcapped
  2. customThe microwave tube was reacted in a microwave reactor (Personel Chemistry, Emrys Optimizer) at 70° C. for 10 minutes
  3. customThe solvent was removed by rotary evaporation
  4. customthe crude product purified via flash column chromatography (SiO2, CH2Cl2:CH3OH 100:0-80:20)

Sources & evidence

ORD record
ord-46c8a1a2cc694283bc5cc4314559f1d9
Source dataset
uspto-grants-2011_12
Patent number
US08071581B2

Reaction notes

Loading…