Cesium carbonate → HCID 68283595, compound

HRID 624007Notes

Reaction equation

HRID 624007 reaction equation
[N+:1]([C:4]1[CH:5]=[N:6][NH:7][CH:8]=1)([O-:3])=[O:2].Br[CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH3:19])[CH:13]=1.C([O-])([O-])=O.[Cs+].[Cs+]>CC#N.C(Cl)Cl>[CH3:19][O:18][C:14]1[CH:13]=[C:12]([CH:17]=[CH:16][CH:15]=1)[CH2:11][CH2:10][N:6]1[CH:5]=[C:4]([N+:1]([O-:3])=[O:2])[CH:8]=[N:7]1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 163764-nitro-1H-pyrazoleHCID 1374501-Bromo-2-(3-methoxyphenyl)ethane

Product 1

HCID 68283595HCID 68283595, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolvent2×HCID 6344DichloromethaneSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 4-nitro-1H-pyrazole (230 mg, 2.03 mmol) in MeCN (9.5 mL), 1-(2-bromo-ethyl)-3-methoxy-benzene (481 mg, 2.24 mmol) dissolved in MeCN (1.5 mL) and Cs2CO3 (729 mg, 2.24 mmol) was added. The resulting mixture was refluxed (80° C.) for 1.5 h, then the reaction mixture was allowed to reach rt. The mixture was diluted with DCM, filtered, the filter cake was washed with DCM and the filtrate was concentrated in vacuo to obtain 1-(3-methoxyphenethyl)-4-nitro-1H-pyrazole as a beige solid which was used in the next step without further purification. LC-MS conditions A: tR=0.86 min, [M+H]+=no ionization.

Workup

  1. customto reach rt
  2. filtrationfiltered
  3. washthe filter cake was washed with DCM
  4. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-07f6a752b0f1423dbf7610b6b87a1af5
Source dataset
uspto-grants-2016_04
Patent number
US09303023B2

Reaction notes

Loading…