Bromine → HCID 58958601, compound

HRID 915570Notes

Reaction equation

HRID 915570 reaction equation
[C:1]([C:5]1[CH:9]=[C:8]([NH2:10])[N:7]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[CH3:17])[N:6]=1)([CH3:4])([CH3:3])[CH3:2].[Br:18]Br>C(O)(=O)C.O>[Br:18][C:9]1[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])=[N:6][N:7]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[CH3:17])[C:8]=1[NH2:10]

Participants

5

Reactant 2

HCID 24408BromineHCID 7706433-tert-Butyl-1-(2-methylphenyl)-1H-pyrazol-5-amine

Product 1

HCID 58958601HCID 58958601, compoundYield 73.3%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

To a solution of 3-tert-butyl-1-(2-methylphenyl)-1H-pyrazol-5-amine (1.00 g, 4.36 mmol) in acetic acid (10 mL) was added bromine (662 mg, 0.21 mL, 4.14 mmol) dropwise. The reaction mixture was stirred for 5 min, and then diluted with water (50 mL), causing a solid to precipitate. The solid was collected by filtration, then dissolved in EtOAc (50 mL). The EtOAc solution was then washed with saturated NaHCO3 and brine, dried (Na2SO4), and concentrated under reduced pressure to afford the product (935 mg, 70%) as a white solid: 1H NMR (300 MHz, DMSO-d6) δ 1.32 (s, 9H), 2.04 (s, 3H) 5.02 (s, 2H), 7.20-7.38 (m, 4H). ES-MS m/z 308.6 (MH+); HPLC RT (min) 3.15.

Workup

  1. customto precipitate
  2. filtrationThe solid was collected by filtration
  3. dissolutiondissolved in EtOAc (50 mL)
  4. washThe EtOAc solution was then washed with saturated NaHCO3 and brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-0e7e3a648507444eb627d8bb04b11a50
Source dataset
uspto-grants-2007_09
Patent number
US07265144B2

Reaction notes

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