Water → HCID 178473413, compound

HRID 1716729Notes

Reaction equation

HRID 1716729 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4]([OH:11])=[N:5][NH:6]2.O.Cl[C:14]([O:16][CH2:17][CH3:18])=[O:15]>N1C=CC=CC=1>[CH2:17]([O:16][C:14]([N:6]1[C:7]2[C:3](=[C:2]([Br:1])[CH:10]=[CH:9][CH:8]=2)[C:4]([OH:11])=[N:5]1)=[O:15])[CH3:18]

Participants

5

Reactant 3

HCID 962WaterHCID 10928Ethyl chloroformateHCID 178518956HCID 178518956, compound

Product 1

HCID 178473413HCID 178473413, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a room temperature suspension of 4-Bromo-1H-indazol-3-ol CLXXXIII (3.19 g, 15.0 mmol) in pyridine (13 ml) and H2O (20 ml) was dropwise added ethyl chloroformate (1.43 ml, 15.0 mmol). After stirring 18 hours at room temperature, the mixture was cooled to 0° C., and the precipitate was filtered and washed with cold AcOH (10 ml in 5 ml of H2O). The solid was dried in vacuo affording 4-Bromo-3-hydroxy-indazole-1-carboxylic acid ethyl ester CLXXXIV as a yellow powder (2.97 g, 69% yield).

Workup

  1. temperaturethe mixture was cooled to 0° C.
  2. filtrationthe precipitate was filtered
  3. washwashed with cold AcOH (10 ml in 5 ml of H2O)
  4. customThe solid was dried in vacuo

Sources & evidence

ORD record
ord-9f0bb4feebb74d5bb9b8743311cab94d
Source dataset
uspto-grants-2010_09
Patent number
US07803830B2

Reaction notes

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