Ethanol → Ethyl 6-bromo-1H-indazole-3-carboxylate

HRID 407153Notes

Reaction equation

HRID 407153 reaction equation
[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:11]([OH:13])=[O:12])=[N:7][NH:8]2)=[CH:4][CH:3]=1.S(Cl)(Cl)=O.[CH2:18](O)[CH3:19]>>[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:11]([O:13][CH2:18][CH3:19])=[O:12])=[N:7][NH:8]2)=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 24386Thionyl ChlorideHCID 247280286-Bromo-1H-indazole-3-carboxylic acid

Product 1

HCID 51358649Ethyl 6-bromo-1H-indazole-3-carboxylate

Procedure

To a stirred solution of 6-bromo-1H-indazole-3-carboxylic acid (5 g, 21 mmol) in ethanol (160 Ml), thionyl chloride (8 Ml, 104 mmol; SOCl2) was added. The mixture was refluxed for 3 h, cooled to room temperature, and concentrated under reduced pressure. Ethyl acetate was added. The organic layer was washed with saturated sodium bicarbonate solution, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by flash column chromatography (silica gel, DCM:MeOH=9:1) to give ethyl 6-bromo-1H-indazole-3-carboxylate (2.8 g).

Workup

  1. temperatureThe mixture was refluxed for 3 h
  2. concentrationconcentrated under reduced pressure
  3. additionEthyl acetate was added
  4. washThe organic layer was washed with saturated sodium bicarbonate solution
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by flash column chromatography (silica gel, DCM:MeOH=9:1)

Sources & evidence

ORD record
ord-8822949004f946debace9372bfdae753
Source dataset
uspto-grants-2014_06
Patent number
US08754209B2

Reaction notes

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