Ammonia → HCID 90308773, compound

HRID 2283685Notes

Reaction equation

HRID 2283685 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]([C:20]([CH3:23])([CH3:22])[CH3:21])[N:15]=2)[CH:11]=1.C(OCC)(=O)C>[Cu](I)I.O.CCCCCC>[C: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)([CH3:23])([CH3:22])[CH3:21]

Participants

8

Reactant 4

HCID 222AmmoniaHCID 8857Ethyl AcetateHCID 13387N-methyl-2-pyrrolidoneHCID 90308823HCID 90308823, compound

Product 1

HCID 90308773HCID 90308773, compound

Reagents, catalysts & solvents 3

HCID 83717Copper iodideCatalystHCID 962WaterSolventHCID 8058HexaneSolvent

Conditions

Temperature
95 °C

Procedure

Copper oxide (I) (2.7 g), NMP (150 mL), and concentrated aqueous ammonia (150 mL) were added to 5-bromo-2-(tert-butyl)-7-methyl-2H-indazole obtained in the above-described Step 1 (40.3 g). The reaction solution was stirred in a portable reactor at 95° C. for 10 hours. The reaction solution was cooled to room temperature, and ethyl acetate (500 mL), hexane (200 mL), and water (300 mL) were added. After separation, the organic layer 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 to obtain 2-(tert-butyl)-7-methyl-2H-indazol-5-amine as a purple solid.

Workup

  1. customobtained in the above-described Step 1 (40.3 g)
  2. temperatureThe reaction solution was cooled to room temperature
  3. customAfter separation
  4. washthe organic layer was washed successively with water four times
  5. dry with materialAfter drying over anhydrous sodium sulfate
  6. customthe solvent was evaporated under vacuum

Sources & evidence

ORD record
ord-4af89238df4744828f461ac3d6d35171
Source dataset
uspto-grants-2015_09
Patent number
US09145414B2

Reaction notes

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