Methanol → Methyl 6-bromo-1H-indazole-3-carboxylate

HRID 1398601Notes

Reaction equation

HRID 1398601 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.[CH3:18]O>>[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:11]([O:13][CH3:18])=[O:12])=[N:7][NH:8]2)=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 247280286-Bromo-1H-indazole-3-carboxylic acid

Product 1

HCID 46784006Methyl 6-bromo-1H-indazole-3-carboxylate

Conditions

Temperature
60 °C

Procedure

To a solution of 6-bromo-1H-indazole-3-carboxylic acid (1.5 g, 6.22 mmol) in methanol (25 mL) was added thionyl chloride (2.26 ml, 31.12 mmol). The mixture was heated at 60° C. for 1 hr. The reaction mixture was cooled and concentrated in vacuo. The crude residue was dissolved in EtOAc (30 mL) and washed with saturated aqueous NaHCO3 (10 mL), water (10 mL) and dried (Na2SO4), filtered and concentrated in vacuo to give the title intermediate: 1H NMR (500 MHz, CDCl3) delta 4.08 (3H, s), 7.44 (1H, d, J=8.6 Hz), 7.89 (1H, s), 8.09 (1H, d, J=8.7 Hz), 11.70 (1H, s); LC-MS: m/z=+254.85/256.75 (M+H)+.

Workup

  1. temperatureThe reaction mixture was cooled
  2. concentrationconcentrated in vacuo
  3. dissolutionThe crude residue was dissolved in EtOAc (30 mL)
  4. washwashed with saturated aqueous NaHCO3 (10 mL), water (10 mL)
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-94d526991b4c4205b3f20f1c5dce0eae
Source dataset
uspto-grants-2014_12
Patent number
US08901313B2

Reaction notes

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