Cesium carbonate → HCID 50999752, compound

HRID 624002Notes

Reaction equation

HRID 624002 reaction equation
[N+:1]([C:4]1[CH:5]=[N:6][NH:7][CH:8]=1)([O-:3])=[O:2].C([O-])([O-])=O.[Cs+].[Cs+].Br[CH2:16][CH2:17][O:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>C(#N)C>[N+:1]([C:4]1[CH:5]=[N:6][N:7]([CH2:16][CH2:17][O:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:8]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 163764-nitro-1H-pyrazoleHCID 68526Benzene, (2-bromoethoxy)-

Product 1

HCID 50999752HCID 50999752, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

To 4-nitro-1H-pyrazole (220 mg, 1.95 mmol) in acetonitrile (10 mL), Cs2CO3 (697 mg, 2.14 mmol) and (2-bromoethoxy)benzene (439 mg, 2.14 mmol) was added. The resulting mixture was refluxed (80° C.) for 40 min and then let stir at rt overnight. The reaction mixture was filtered, the filter cake washed with DCM and the filtrate concentrated in vacuo to obtain 4-nitro-1-(2-phenoxyethyl)-1H-pyrazole as a crude solid which was used without further purification. LC-MS conditions A: tR=0.85 min, [M+H]+=no ionization.

Workup

  1. filtrationThe reaction mixture was filtered
  2. washthe filter cake washed with DCM
  3. concentrationthe filtrate concentrated in vacuo

Sources & evidence

ORD record
ord-bd390306c7d14248ac98f58255c23c3b
Source dataset
uspto-grants-2016_04
Patent number
US09303023B2

Reaction notes

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