Bromine → 4-bromo-3-tert-butyl-1-(2-methoxy-6-methylphenyl)-1H-pyrazol-5-amine

HRID 2109929Notes

Reaction equation

HRID 2109929 reaction equation
[C:1]([C:5]1[CH:9]=[C:8]([NH2:10])[N:7]([C:11]2[C:16]([CH3:17])=[CH:15][CH:14]=[CH:13][C:12]=2[O:18][CH3:19])[N:6]=1)([CH3:4])([CH3:3])[CH3:2].[Br:20]Br>C(O)(=O)C.O>[Br:20][C:9]1[C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])=[N:6][N:7]([C:11]2[C:16]([CH3:17])=[CH:15][CH:14]=[CH:13][C:12]=2[O:18][CH3:19])[C:8]=1[NH2:10]

Participants

5

Reactant 2

HCID 24408BromineHCID 576357753-Tert-butyl-1-(2-methoxy-6-methylphenyl)-1h-pyrazol-5-amine2×

Product 1

HCID 576358774-bromo-3-tert-butyl-1-(2-methoxy-6-methylphenyl)-1H-pyrazol-5-amineYield 108.2%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

To a solution of 3-tert-butyl-1-(2-methoxy-6-methylphenyl)-1H-pyrazol-5-amine (2.00 g, 7.71 mmol) (Intermediate C) in acetic acid (15 mL) was added bromine (1170 mg, 0.38 mL, 7.33 mmol) dropwise. The reaction mixture was stirred for 5 min at rt, and then diluted with water (100 mL), causing a solid to precipitate. The solid was collected by filtration, then dissolved in EtOAc. The organic phase was then washed with saturated NaHCO3 and brine, dried (Na2SO4), filtered, and concentrated under reduced pressure to afford product (2683 mg, 102%) containing minor impurities. ES-MS m/z 338.2 (MH+); HPLC RT (min) 3.06.

Workup

  1. customto precipitate
  2. filtrationThe solid was collected by filtration
  3. dissolutiondissolved in EtOAc
  4. washThe organic phase was then washed with saturated NaHCO3 and brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-75ff4f5f7ddb44b0aaab6d0fc53400d0
Source dataset
uspto-grants-2009_04
Patent number
US07517878B2

Reaction notes

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