Cesium carbonate → 1-methyl-6-(4-((1-(4-methylpyridin-2-yl)piperidin-4-yl)methoxy)-3-(trifluoromethyl)phenyl)-1H-[1,2,3]triazolo[4,5-c]pyridine-4-carbonitrile

HRID 517955Notes

Reaction equation

HRID 517955 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:13]=[C:12]([C:14]#[N:15])[C:11]3[N:16]=[N:17][N:18]([CH3:19])[C:10]=3[CH:9]=2)=[CH:4][C:3]=1[C:20]([F:23])([F:22])[F:21].CS(O[CH2:29][CH:30]1[CH2:35][CH2:34][N:33]([C:36]2[CH:41]=[C:40]([CH3:42])[CH:39]=[CH:38][N:37]=2)[CH2:32][CH2:31]1)(=O)=O.C(=O)([O-])[O-].[Cs+].[Cs+]>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C=O)C.C(OCC)(=O)C>[CH3:19][N:18]1[C:10]2[CH:9]=[C:8]([C:5]3[CH:6]=[CH:7][C:2]([O:1][CH2:29][CH:30]4[CH2:35][CH2:34][N:33]([C:36]5[CH:41]=[C:40]([CH3:42])[CH:39]=[CH:38][N:37]=5)[CH2:32][CH2:31]4)=[C:3]([C:20]([F:23])([F:22])[F:21])[CH:4]=3)[N:13]=[C:12]([C:14]#[N:15])[C:11]=2[N:16]=[N:17]1

Participants

7

Reactant 3

HCID 10796Cesium carbonateHCID 86673349(1-(4-Methylpyridin-2-yl)piperidin-4-yl)methyl methanesulfonateHCID 1363523116-(4-hydroxy-3-(trifluoromethyl)-phenyl)-1-methyl-1H-[1,2,3]triazolo[4,5-c]pyridine-4-carbonitrile

Product 1

HCID 672944701-methyl-6-(4-((1-(4-methylpyridin-2-yl)piperidin-4-yl)methoxy)-3-(trifluoromethyl)phenyl)-1H-[1,2,3]triazolo[4,5-c]pyridine-4-carbonitrile

Reagents, catalysts & solvents 3

HCID 67553Tetrabutylammonium IodideCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

6-(4-Hydroxy-3-(trifluoromethyl)phenyl)-1-methyl-1H-[1,2,3]triazolo[4,5-c]pyridine-4-carbonitrile (0.626 mmol, 0.2 g), (1-(4-methylpyridin-2-yl)piperidin-4-yl)methyl methanesulfonate (0.752 mmol, 0.214 g), cesium carbonate (0.940 mmol, 0.306 g) and tetrabutylammonium iodide (0.313 mmol, 0.116 g) were stirred in DMF (1 ml) at 50° C. overnight. The reaction mixture was diluted with ethyl acetate, washed with water and dried over Na2SO4. The resulting residue was triturated with ether and filtered. The solid was sonicated in methanol, filtered and dried to afford 1-methyl-6-(4-((1-(4-methylpyridin-2-yl)piperidin-4-yl)methoxy)-3-(trifluoromethyl)phenyl)-1H-[1,2,3]triazolo[4,5-c]pyridine-4-carbonitrile. (134 mg)

Workup

  1. washwashed with water
  2. dry with materialdried over Na2SO4
  3. customThe resulting residue was triturated with ether
  4. filtrationfiltered
  5. customThe solid was sonicated in methanol
  6. filtrationfiltered
  7. customdried

Sources & evidence

ORD record
ord-0062adda6d6a425b83fd8cd04bbef92a
Source dataset
uspto-grants-2015_08
Patent number
US09115126B2

Reaction notes

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