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

HRID 505506Notes

Reaction equation

HRID 505506 reaction equation
FC1C=CC=CC=1C=O.[Br:10][C:11]1[CH:12]=[C:13]([CH:25]=[C:26]([Cl:28])[CH:27]=1)[O:14][C:15]1[C:22]([Cl:23])=[CH:21][CH:20]=[C:19](F)[C:16]=1[CH:17]=O.O.[NH2:30][NH2:31]>CS(C)=O>[Br:10][C:11]1[CH:12]=[C:13]([CH:25]=[C:26]([Cl:28])[CH:27]=1)[O:14][C:15]1[C:22]([Cl:23])=[CH:21][CH:20]=[C:19]2[C:16]=1[CH:17]=[N:30][NH:31]2

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 866244702-(3-Bromo-5-chlorophenoxy)-3-chloro-6-fluorobenzaldehyde fluorobenzaldehyde

Product 1

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

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A suspension of 2-(3-bromo-5-chlorophenoxy)-3-chloro-6-fluorobenzaldehyde fluorobenzaldehyde (4.5 kg; 12.36 moles; 1.0 eq.) in DMSO (18 L) was degassed, after which hydrazine monohydrate (6.192 kg; 123.7 moles; 10.0 eqs.) was added over 20 minutes at room temperature. The reaction solution was degassed again, stirred at room temperature for 15 minutes, heated to 73° C., and then aged for 16 hours. After the mixture was cooled to room temperature, isopropanol (15 L) and then water (40 L) were added, and the resulting mixture cooled to room temperature, filtered under pressure, and washed with isopropanol:water (1:2; 10 L), water (12 L), and heptane (12 L). The title product as a solid was obtained after drying at 30° C.-35° C. under vacuum for four days.

Workup

  1. customwas degassed
  2. customThe reaction solution was degassed again
  3. temperatureheated to 73° C.
  4. waitaged for 16 hours
  5. temperatureAfter the mixture was cooled to room temperature
  6. additionisopropanol (15 L) and then water (40 L) were added
  7. temperaturethe resulting mixture cooled to room temperature
  8. filtrationfiltered under pressure
  9. washwashed with isopropanol:water (1:2; 10 L), water (12 L), and heptane (12 L)

Sources & evidence

ORD record
ord-3e5c46afdb11497aa17d5232d9467c19
Source dataset
uspto-grants-2010_08
Patent number
US07781454B2

Reaction notes

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