Potassium Carbonate → 1-(2-Methoxyethyl)-4-nitro-1H-pyrazole

HRID 1487639Notes

Reaction equation

HRID 1487639 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][CH3:13].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH3:13][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

5

Reactant 3

HCID 11430Potassium CarbonateHCID 163764-nitro-1H-pyrazoleHCID 809722-Bromoethyl methyl ether

Product 1

HCID 578205541-(2-Methoxyethyl)-4-nitro-1H-pyrazoleYield 76%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 4-nitro-1H-pyrazole (1 equiv), 1-bromo-2-methoxyethane (1.05 equiv), potassium carbonate (1.5 equiv) and acetonitrile (0.44 M) was stirred and heated to 60° C. for 6 h. The resultant mixture was evaporated and the residue was purified by flash chromatography (2.5% MeOH in DCM) to afford the desired product as a yellow solid (76% yield). 1H NMR (400 MHz, CHLOROFORM-d1) δ ppm 8.25 (s, 1H), 8.08 (s, 1H), 4.34-4.31 (t, J=4.8 Hz, 2H), 3.77-3.74 (t, J=4.8 Hz, 2H), 3.37 (s, 3H).

Workup

  1. customThe resultant mixture was evaporated
  2. customthe residue was purified by flash chromatography (2.5% MeOH in DCM)

Sources & evidence

ORD record
ord-ea078bfc97cf47bfb875ac941c94c9df
Source dataset
uspto-grants-2016_08
Patent number
US09428509B2

Reaction notes

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