Hydrazine hydrate (1:1) → HCID 66977301, compound

HRID 712365Notes

Reaction equation

HRID 712365 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([N:8]2[CH:12]=[CH:11][CH:10]=[N:9]2)[N:5]2[CH:13]=[C:14]([C:16]([O:18]CC)=O)[N:15]=[C:4]2[CH:3]=1.O.[NH2:22][NH2:23]>CCO>[Br:1][C:2]1[CH:7]=[C:6]([N:8]2[CH:12]=[CH:11][CH:10]=[N:9]2)[N:5]2[CH:13]=[C:14]([C:16]([NH:22][NH2:23])=[O:18])[N:15]=[C:4]2[CH:3]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 66977306HCID 66977306, compound

Product 1

HCID 66977301HCID 66977301, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a suspension of ethyl 7-bromo-5-pyrazol-1-yl-imidazo[1,2-a]pyridine-2-carboxylate (3.96 g, 11.8 mmol) in EtOH (100 mL) was added hydrazine hydrate (5.91 mL, 0.118 mmol) and the mixture stirred overnight at rt. After 3 days, the reaction was almost complete by LCMS so stirring was maintained for 1 more night. The mixture was diluted with EtOH (50 mL), filtered and the solids washed with EtOH (2×50 mL), EtOAc (2×50 mL) and heptane (50 mL) before being air dried. The yield was 3.56 g (94%) LCMS MS: 321.01, 322.98 [M+H]+.

Workup

  1. waitAfter 3 days
  2. stirringso stirring
  3. temperaturewas maintained for 1 more night
  4. filtrationfiltered
  5. washthe solids washed with EtOH (2×50 mL), EtOAc (2×50 mL) and heptane (50 mL)
  6. customdried

Sources & evidence

ORD record
ord-e79bcfdb8aa640d78c68882d6a724ebf
Source dataset
uspto-grants-2015_11
Patent number
US09181234B2

Reaction notes

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