Chloroacetyl chloride → 6-Bromo-4-[5-(chloromethyl)-1,3,4-oxadiazol-2-yl]-1-methyl-1H-indazole

HRID 520526Notes

Reaction equation

HRID 520526 reaction equation
[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[N:7][N:8]2[CH3:11])=[C:4]([C:12]2[NH:16][N:15]=NN=2)[CH:3]=1.[Cl:17][CH2:18][C:19](Cl)=[O:20]>C(Cl)(Cl)Cl>[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[N:7][N:8]2[CH3:11])=[C:4]([C:12]2[O:20][C:19]([CH2:18][Cl:17])=[N:15][N:16]=2)[CH:3]=1

Participants

4

Reactant 2

HCID 6577Chloroacetyl chloride2×HCID 178481726HCID 178481726, compound

Product 1

HCID 667771726-Bromo-4-[5-(chloromethyl)-1,3,4-oxadiazol-2-yl]-1-methyl-1H-indazoleYield 74.4%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
110 °C

Procedure

6-Bromo-1-methyl-4-(1H-tetrazol-5-yl)-1H-indazole (604.6 mg, 2.166 mmol) was dissolved in chloroform (20 ml). Chloroacetyl chloride (0.520 ml, 6.49 mmol) was added and the mixture stirred at 110° C. for 46 h. Further chloroacetyl chloride (0.174 ml, 2.166 mmol) was added and the reaction continued stirred at 110° C. for 26 h. The reaction mixture was cooled and the solvent removed in vacuo. The resultant white solid was washed with DCM, the solvent removed under vacuum and the solid dried under high vacuum for 18 h to give the title compound as a white solid (528 mg).

Workup

  1. stirringthe reaction continued stirred at 110° C. for 26 h
  2. temperatureThe reaction mixture was cooled
  3. customthe solvent removed in vacuo
  4. washThe resultant white solid was washed with DCM
  5. customthe solvent removed under vacuum
  6. customthe solid dried under high vacuum for 18 h

Sources & evidence

ORD record
ord-8dfc350458a148b29f94eecd8eec29f5
Source dataset
uspto-grants-2016_05
Patent number
US09326987B2

Reaction notes

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