Water → HCID 86694714, compound

HRID 475166Notes

Reaction equation

HRID 475166 reaction equation
C([O:3][C:4]([C:6]1[CH:14]=[C:13]([F:15])[CH:12]=[C:11]2[C:7]=1[CH:8]=[N:9][N:10]2[CH3:16])=[CH2:5])C.O>C1COCC1.Cl>[F:15][C:13]1[CH:12]=[C:11]2[C:7]([CH:8]=[N:9][N:10]2[CH3:16])=[C:6]([C:4](=[O:3])[CH3:5])[CH:14]=1

Participants

5

Reactant 2

HCID 962WaterHCID 86694713HCID 86694713, compound

Product 1

HCID 86694714HCID 86694714, compoundYield 55.6%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4-(1-ethoxyvinyl)-6-fluoro-1-methyl-1H-indazole (1.24 g, 5.62 mmol) in THF (10 mL) and aqueous HCl (2.0 N, 10 mL) was stirred at RT for 2 h then poured into water (200 mL) and extracted with EtOAc (2×50 mL). The combined extracts were washed with an aqueous NH4OH (30 mL) and brine (50 mL), dried (MgSO4), filtered, and evaporated in vacuo to afford 1-(6-fluoro-1-methyl-1H-indazol-4-yl)ethanone as a white solid (600 mg, 55%). MS (ESI): m/z=193.2 [M+1]+.

Workup

  1. extractionextracted with EtOAc (2×50 mL)
  2. washThe combined extracts were washed with an aqueous NH4OH (30 mL) and brine (50 mL)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-0dcd8a91f1214f53924383d182d47fa5
Source dataset
uspto-grants-2014_01
Patent number
US08637537B2

Reaction notes

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