Bromine → Ethyl 5-[4-(benzyloxy)phenyl]-4-bromo-1-cyclohexyl-1h-pyrazole-3-carboxylate

HRID 2216523Notes

Reaction equation

HRID 2216523 reaction equation
[Br:1]Br.[CH:3]1([N:9]2[C:13]([C:14]3[CH:19]=[CH:18][C:17]([O:20][CH2:21][C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)=[CH:16][CH:15]=3)=[CH:12][C:11]([C:28]([O:30][CH2:31][CH3:32])=[O:29])=[N:10]2)[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1>CC(O)=O>[CH2:21]([O:20][C:17]1[CH:18]=[CH:19][C:14]([C:13]2[N:9]([CH:3]3[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]3)[N:10]=[C:11]([C:28]([O:30][CH2:31][CH3:32])=[O:29])[C:12]=2[Br:1])=[CH:15][CH:16]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

4

Reactant 2

HCID 24408BromineHCID 11327171Ethyl 1-cyclohexyl-5-(4-benzyloxyphenyl)-1H-pyrazole-3-carboxylate

Product 1

HCID 11340655Ethyl 5-[4-(benzyloxy)phenyl]-4-bromo-1-cyclohexyl-1h-pyrazole-3-carboxylateYield 62%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Bromine (82 μL, 1.61 mmol) was added to pyrazole 1.3 (500 mg, 1.24 mmol) in AcOH (5 ml) at 0° C. and the reaction mixture was stirred at rt for 17 h. Upon concentration, the crude product was purified by SiO2 chromatography (stepwise gradient: 20 to 25% EtOAc/hexanes) to afford 368 mg (62%) of bromide 8.1. MS (ESI) 483.4 (MH+).

Workup

  1. concentrationUpon concentration
  2. customthe crude product was purified by SiO2 chromatography (stepwise gradient

Sources & evidence

ORD record
ord-31ecac3209db49f2ba1c19eb80aa46ec
Source dataset
uspto-grants-2006_09
Patent number
US07112601B2

Reaction notes

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