Water → HCID 19737204, compound

HRID 258257Notes

Reaction equation

HRID 258257 reaction equation
[Cl:1][C:2]1[C:3]([N:12]2[C:20]3[C:15]([CH:16]=[C:17]4[N:23]=[N:22][N:21]=[C:18]4[CH:19]=3)=[CH:14][NH:13]2)=[N:4][CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.Br[CH:25]([CH3:30])[C:26]([O:28][CH3:29])=[O:27].C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[Cl:1][C:2]1[C:3]([N:12]2[C:20]3[CH:19]=[C:18]4[N:21]([CH:25]([C:26]([O:28][CH3:29])=[O:27])[CH3:30])[N:22]=[N:23][C:17]4=[CH:16][C:15]=3[CH:14]=[N:13]2)=[N:4][CH:5]=[C:6]([C:8]([F:10])([F:9])[F:11])[CH:7]=1.[Cl:1][C:2]1[C:3]([N:12]2[C:20]3[CH:19]=[C:18]4[N:21]=[N:22][N:23]([CH:25]([C:26]([O:28][CH3:29])=[O:27])[CH3:30])[C:17]4=[CH:16][C:15]=3[CH:14]=[N:13]2)=[N:4][CH:5]=[C:6]([C:8]([F:10])([F:9])[F:11])[CH:7]=1

Participants

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 95576Methyl 2-bromopropionateHCID 178506244HCID 178506244, compound

Product 2

HCID 19737204HCID 19737204, compoundHCID 19737205HCID 19737205, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-(3-chloro-5-trifluoromethylpyridin-2-yl)[1,2,3]triazolo[4,5-f]indazole [Compound No. 48] (1.0 g) in N,N-dimethylformamide (10 g), methyl 2-bromopropionate (0.5 g) and potassium carbonate (1 g) were added, and the resultant mixture was stirred at 40° C. for 3 hours. After completion of the reaction, the reaction mixture was poured into water and extracted with ethyl acetate. The extract was washed, dried over magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography with hexane-ethyl acetate (4:1) to give 5-(3-chloro-5-trifluoromethylpyridin-2-yl)-3-(1-methoxycarbonylethyl)[1,2,3]triazolo[4,5-f]indazole (0.3 g) and 5-(3-chloro-5-trifluoromethylpyridin-2-yl)-1-(1-methoxycarbonylethyl)[1,2,3]triazolo[4,5-f]indazole (0.1 g).

Workup

  1. customAfter completion of the reaction
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography with hexane-ethyl acetate (4:1)

Sources & evidence

ORD record
ord-89091551cdc042e1b4eaf81ecb2d4369
Source dataset
uspto-grants-1993_11
Patent number
US05266556

Reaction notes

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