Water → HCID 19737192, compound

HRID 258252Notes

Reaction equation

HRID 258252 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[C:4]([Cl:12])[C:3]=1[N:13]1[C:21]2[C:16](=[CH:17][CH:18]=[C:19]([OH:22])[CH:20]=2)[CH:15]=[N:14]1.C(N(CC)CC)C.[CH3:30][O:31][C:32](Cl)=[O:33].O>ClCCl>[C:32](=[O:33])([O:22][C:19]1[CH:20]=[C:21]2[C:16]([CH:15]=[N:14][N:13]2[C:3]2[C:2]([Cl:1])=[CH:7][C:6]([C:8]([F:10])([F:9])[F:11])=[CH:5][C:4]=2[Cl:12])=[CH:17][CH:18]=1)[O:31][CH3:30]

Participants

6

Reactant 4

HCID 962WaterHCID 6586Methyl chloroformateHCID 8471TriethylamineHCID 135749814HCID 135749814, compound

Product 1

HCID 19737192HCID 19737192, compoundYield 94.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-(2,6-dichloro-4-trifluoromethylphenyl)-6-hydroxyindazole [Compound No. 80] (10 g) in dichloromethane (30 ml), triethylamine (5 g) and methoxycarbonyl chloride (7 g) were added, and the resultant mixture was refluxed for 3 hours. After completion of the reaction, the reaction mixture was poured into water and extracted with diethyl ether. The extract was washed with water, 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 methyl 1-(2,6-dichloro-4-trifluoromethylphenyl)indazol-6-yl carbonate (11 g).

Workup

  1. customAfter completion of the reaction
  2. extractionextracted with diethyl ether
  3. washThe extract was washed with water
  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-af33d9fcf89d49e1b5e2a000de8975f0
Source dataset
uspto-grants-1993_11
Patent number
US05266556

Reaction notes

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