Cesium carbonate → HCID 68283466, compound

HRID 624009Notes

Reaction equation

HRID 624009 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][O:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH3:20])[CH:14]=1.C([O-])([O-])=O.[Cs+].[Cs+]>CC#N.C(Cl)Cl>[CH3:20][O:19][C:15]1[CH:14]=[C:13]([CH:18]=[CH:17][CH:16]=1)[O:12][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 22454291-(2-bromoethoxy)-3-methoxybenzene

Product 1

HCID 68283466HCID 68283466, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolvent2×HCID 6344DichloromethaneSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 4-nitro-1H-pyrazole (220 mg, 1.90 mmol) in MeCN (9.5 mL), 1-(2-bromoethoxy)-3-methoxybenzene (495 mg, 2.14 mmol) dissolved in MeCN (1.5 mL) and Cs2CO3 (697 mg, 2.14 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-(2-(3-methoxyphenoxy)ethyl)-4-nitro-1H-pyrazole which was used in the next step without further purification. LC-MS conditions A: tR=0.85 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-33e9cdd448984706935ea448b2384189
Source dataset
uspto-grants-2016_04
Patent number
US09303023B2

Reaction notes

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