Ammonia → HCID 90309187, compound

HRID 2283698Notes

Reaction equation

HRID 2283698 reaction equation
C[N:2]1C(=O)CCC1.N.Br[C:10]1[CH:18]=[C:17]([CH3:19])[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>[CH2:20]([N:14]1[CH:13]=[C:12]2[C:16]([C:17]([CH3:19])=[CH:18][C:10]([NH2:2])=[CH:11]2)=[N:15]1)[CH3:21]

Participants

6

Reactant 3

HCID 222AmmoniaHCID 13387N-methyl-2-pyrrolidoneHCID 90308704HCID 90308704, compound

Product 1

HCID 90309187HCID 90309187, compound

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

Copper oxide (I) (60 mg), NMP (2 mL), and concentrated aqueous ammonia (2 mL) were added to 5-bromo-2-ethyl-7-methyl-2H-indazole obtained in the above-described Step 1 (446 mg), and the reaction solution was stirred in a microwave reactor at 100° 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. The resultant residue was purified by column chromatography on silica gel (developing solvent:hexane/ethyl acetate) to obtain 2-ethyl-7-methyl-2H-indazol-5-amine.

Workup

  1. customobtained in the above-described Step 1 (446 mg)
  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 residue was purified by column chromatography on silica gel (developing solvent:hexane/ethyl acetate)

Sources & evidence

ORD record
ord-011044f2a309401cae11c153b08d8c9b
Source dataset
uspto-grants-2015_09
Patent number
US09145414B2

Reaction notes

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