Diethyl Ether → HCID 67120049, compound

HRID 1410145Notes

Reaction equation

HRID 1410145 reaction equation
[NH2:1][C:2]1[N:6]([C:7]2[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[CH:9][CH:8]=2)[N:5]=[C:4]([CH2:15][CH3:16])[C:3]=1[C:17]#[N:18].[Li+].[CH3:20][CH:21]([N-]C(C)C)C.C(Br)C.CCOCC>C1COCC1.O>[CH2:15]([C:4]1[C:3]([C:17]#[N:18])=[C:2]([NH:1][CH2:20][CH3:21])[N:6]([C:7]2[CH:8]=[CH:9][C:10]([O:13][CH3:14])=[CH:11][CH:12]=2)[N:5]=1)[CH3:16]

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 6332Ethyl BromideHCID 2724682Lithium diisopropylamideHCID 68156597HCID 68156597, compound

Product 1

HCID 67120049HCID 67120049, compoundYield 23.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To 5-amino-3-ethyl-1-(4-methoxyphenyl)-1H-pyrazole-4-carbonitrile (0.50 g, 2.06 mmol) in THF (10 mL) at −78 C was added LDA (0.6 M in THF, 4.5 mL, 2.7 mmol) and stirred for 5 min, followed by EtBr (500 μL, 6.81 mmol) and the reaction was stirred over night at room temperature. Et2O and water were added, and the organic phase was separated. The water phase was acidified using 1 M HCl which was extracted with EtOAc. After drying using MgSO4, and evaporation of solvent the crude was purified using silica chromatography to give 3-ethyl-5-(ethylamino)-1-(4-methoxyphenyl)-1H-pyrazole-4-carbonitrile (130 mg, 23%).

Workup

  1. stirringthe reaction was stirred over night at room temperature
  2. customthe organic phase was separated
  3. extractionwas extracted with EtOAc
  4. customAfter drying
  5. customMgSO4, and evaporation of solvent the crude
  6. customwas purified

Sources & evidence

ORD record
ord-3543ec459079404489a0941ffbcbbcea
Source dataset
uspto-grants-2014_12
Patent number
US08921402B2

Reaction notes

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