Ammonia → HCID 90308680, compound

HRID 2283702Notes

Reaction equation

HRID 2283702 reaction equation
C[N:2]1C(=O)CCC1.N.Br[C:10]1[CH:18]=[C:17]([Cl:19])[C:16]2[C:12](=[CH:13][N:14]([CH2:20][CH3:21])[N:15]=2)[CH:11]=1>C(OCC)(=O)C.[Cu](I)I>[Cl:19][C:17]1[C:16]2[C:12](=[CH:13][N:14]([CH2:20][CH3:21])[N:15]=2)[CH:11]=[C:10]([NH2:2])[CH:18]=1

Participants

6

Reactant 3

HCID 222AmmoniaHCID 13387N-methyl-2-pyrrolidoneHCID 90308796HCID 90308796, compound

Product 1

HCID 90308680HCID 90308680, compound

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

Copper oxide (I) (200 mg), NMP (7 mL), and concentrated aqueous ammonia (7 mL) were added to 5-bromo-7-chloro-2-ethyl-2H-indazole obtained in the above-described Step 1 (1.43 g), and the reaction solution was stirred in a microwave reactor at 80° C. for 10 hours. The reaction solution was cooled to room temperature, and diluted with ethyl acetate. Thereafter, the reaction solution was washed successively with water four times and then with a saturated saline solution. After drying over anhydrous sodium sulfate, the solvent was evaporated under vacuum, and the resultant was purified by column chromatography on silica gel (developing solvent:hexane/ethyl acetate) to obtain 7-chloro-2-ethyl-2H-indazol-5-amine.

Workup

  1. customobtained in the above-described Step 1 (1.43 g)
  2. temperatureThe reaction solution was cooled to room temperature
  3. washThereafter, the reaction solution was washed successively with water four times
  4. dry with materialAfter drying over anhydrous sodium sulfate
  5. customthe solvent was evaporated under vacuum
  6. customthe resultant was purified by column chromatography on silica gel (developing solvent:hexane/ethyl acetate)

Sources & evidence

ORD record
ord-564cf17002cf46b0ab278317de3756a7
Source dataset
uspto-grants-2015_09
Patent number
US09145414B2

Reaction notes

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