Potassium Carbonate → Tert-butyl 2-(3-carbamoyl-1H-indazol-1-yl)acetate

HRID 1527286Notes

Reaction equation

HRID 1527286 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([C:10]([NH2:12])=[O: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:11])[NH2:12]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 79177tert-Butyl bromoacetateHCID 209781761H-Indazole-3-carboxamide

Product 1

HCID 68283122Tert-butyl 2-(3-carbamoyl-1H-indazol-1-yl)acetate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a suspension of 1H-indazole-3-carboxamide [90004-04-9] (2.00 g, 12.4 mmol) and potassium carbonate (4.12 g, 29.8 mmol) in CH3CN (60 mL) was added tert-butyl bromoacetate (2.20 mL, 14.9 mmol) dropwise at RT, and the resulting mixture was heated to reflux for 16 h. The mixture was then cooled to RT and filtered, the solid was washed with CH3CN and the filtrate was concentrated under vacuum. The residual oil was used directly in the next reaction step without further purification. MS (LC/MS): 276.0 [M+H]+; tR (HPLC conditions k): 3.22 min.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureto reflux for 16 h
  3. filtrationfiltered
  4. washthe solid was washed with CH3CN
  5. concentrationthe filtrate was concentrated under vacuum
  6. customThe residual oil was used directly in the next reaction step without further purification
  7. custom3.22 min.

Sources & evidence

ORD record
ord-a63fad99920b4b25b58bd53160f63a8a
Source dataset
uspto-grants-2015_07
Patent number
US09085555B2

Reaction notes

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