Potassium Carbonate → tert-butyl 2-(3-acetyl-1H-indazol-1-yl)acetate

HRID 1052097Notes

Reaction equation

HRID 1052097 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([C:10](=[O:12])[CH3:11])=[N:2]1.C([O-])([O-])=O.[K+].[K+].Br[CH2:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22]>CC#N>[C:10]([C:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[N:1]([CH2:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[N:2]=1)(=[O:12])[CH3:11]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 79177tert-Butyl bromoacetateHCID 156841691-(1H-indazol-3-yl)ethan-1-one

Product 1

HCID 68283733tert-butyl 2-(3-acetyl-1H-indazol-1-yl)acetate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 1-(1H-indazol-3-yl)ethanone [4498-72-0](2 g, 12.46 mmol) in CH3CN (50 mL) was added K2CO3 (3.97 g, 28.7 mmol) and tert-butyl 2-bromoacetate (2.58 mL, 17.48 mmol). The reaction mixture was stirred at 90° C. overnight. The reaction mixture was filtered, the residue was washed with CH3CN and the filtrate was concentrated under vacuum. The material thus obtained was used directly in the next step without further purification. MS: 275 [M+H]+; tR (HPLC conditions d): 3.78 min.

Workup

  1. filtrationThe reaction mixture was filtered
  2. washthe residue was washed with CH3CN
  3. concentrationthe filtrate was concentrated under vacuum
  4. customThe material thus obtained
  5. customwas used directly in the next step without further purification
  6. custom3.78 min.

Sources & evidence

ORD record
ord-f8492ef54865488ab95c427deb04f006
Source dataset
uspto-grants-2016_07
Patent number
US09388199B2

Reaction notes

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