Hydrazine hydrate (1:1) → 4-(3-bromo-5-chlorophenoxy)-5-chloro-1H-indazole

HRID 505503Notes

Reaction equation

HRID 505503 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:16]=[C:17]([Cl:19])[CH:18]=1)[O:5][C:6]1[C:13]([Cl:14])=[CH:12][CH:11]=[C:10](F)[C:7]=1[CH:8]=O.O.[NH2:21][NH2:22]>C(O)C.O>[Br:1][C:2]1[CH:3]=[C:4]([CH:16]=[C:17]([Cl:19])[CH:18]=1)[O:5][C:6]1[C:13]([Cl:14])=[CH:12][CH:11]=[C:10]2[C:7]=1[CH:8]=[N:21][NH:22]2

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 568335532-(3-Bromo-5-chlorophenoxy)-3-chloro-6-fluorobenzaldehyde

Product 1

HCID 568336424-(3-bromo-5-chlorophenoxy)-5-chloro-1H-indazole

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a suspension of 2-(3-bromo-5-chlorophenoxy)-3-chloro-6-fluorobenzaldehyde (77.5 g, 213 mmol) in ethanol (120 mL) was added hydrazine hydrate (31 mL, 639 mmol). The resulting mixture was then heated at reflux for 4 days, after which the mixture was cooled to room temperature, diluted with water (100 mL) and the resulting solid was filtered. The solid was absorbed onto silica gel (300 g) and purified on a silica gel (1500 g) column (0-40% EtOAc/CH2Cl2) to give the title product as a white solid. LRMS (M+1)=358.8

Workup

  1. temperatureThe resulting mixture was then heated
  2. temperatureat reflux for 4 days
  3. filtrationthe resulting solid was filtered
  4. customThe solid was absorbed onto silica gel (300 g)
  5. custompurified on a silica gel (1500 g) column (0-40% EtOAc/CH2Cl2)

Sources & evidence

ORD record
ord-2e3984c1570c4926a5f81b4cf3bf093c
Source dataset
uspto-grants-2010_08
Patent number
US07781454B2

Reaction notes

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