Acetic Anhydride → 1-(5-Bromo-3-methyl-1H-indazol-1-yl)ethan-1-one

HRID 240772Notes

Reaction equation

HRID 240772 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][N:6]=[C:5]2[CH3:11].[C:12](OC(=O)C)(=[O:14])[CH3:13]>C(Cl)Cl.C(N(C(C)C)CC)(C)C.C(OCC)(=O)C>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([C:12](=[O:14])[CH3:13])[N:6]=[C:5]2[CH3:11]

Participants

6

Reactant 2

HCID 7918Acetic AnhydrideHCID 178434225HCID 178434225, compound

Product 1

HCID 591273821-(5-Bromo-3-methyl-1H-indazol-1-yl)ethan-1-one

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolventHCID 81531DiisopropylethylamineSolvent

Procedure

5-Bromo-3-methyl-1H-indazole (838 mg, 3.97 mmol) was dissolved in methylene chloride (15 mL) and diisopropylethylamine (0.7 mL). Acetic anhydride (500 μL, 5.29 mmol) was added and the mixture was stirred at ambient temperature overnight. The mixture was diluted with ethyl acetate, washed with 1 N sodium hydroxide followed by 1 N hydrochloric acid and then brine. The organic layer was dried over sodium sulfate and the solvent was removed under reduced pressure to afford the title compound. MS (ESI+) m/z 252.7 (M+H)+.

Workup

  1. washwashed with 1 N sodium hydroxide
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-0cfb0541e983429d8f68a543dc133873
Source dataset
uspto-grants-2014_02
Patent number
US08648069B2

Reaction notes

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