Potassium Carbonate → HCID 114798686, compound

HRID 1509649Notes

Reaction equation

HRID 1509649 reaction equation
[C:1]1([C:7]2[CH:8]=[N:9][NH:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.I[C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH3:20])[CH:14]=1.C([O-])([O-])=O.[K+].[K+].[C@@H]1(N)CCCC[C@H]1N>O1CCOCC1.[Cu]I>[CH3:20][O:19][C:15]1[CH:14]=[C:13]([N:9]2[CH:8]=[C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[CH:11]=[N:10]2)[CH:18]=[CH:17][CH:16]=1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 438061,2-Diaminocyclohexane, trans-HCID 69839Benzene, 1-iodo-3-methoxy-HCID 1391064-Phenylpyrazole

Product 1

HCID 114798686HCID 114798686, compound

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 4-phenyl-1H-pyrazole (775 mg, 5.38 mmol, 1.0 eq), 1-iodo-3-methoxybenzene (1510 mg, 768 μL, 6.45 mmol, 1.2 eq), CuI (21 mg, 0.11 mmol, 0.02 eq), K2CO3 (1561 mg, 11.30 mmol, 2.1 eq) and trans-1,2-cyclohexanediamine (123 mg, 1.08 mmol, 0.20 eq) in dioxane (12 mL) was stirred at a temperature of 110° C. for three days, then cooled to ambient temperature. The solvent was removed under reduced pressure and the residue was purified through column chromatography on silica gel using hexane and ethyl acetate (10:1-5:1-3:1) as an eluent to obtain the desired product, 1-(3-methoxyphenyl)-4-phenyl-1H-pyrazole 5, as a colorless liquid (1.13 g in 84% yield). 1H NMR (DMSO-d6, 400 MHz): δ 3.84 (s, 3H), 6.87-6.90 (m, 1H), 7.25 (t, J=7.2 Hz, 1H), 7.38-7.48 (m, 5H), 7.71 (d, J=7.2 Hz, 2H), 8.20 (s, 1H), 9.01 (s, 1H).

Workup

  1. temperaturecooled to ambient temperature
  2. customThe solvent was removed under reduced pressure
  3. customthe residue was purified through column chromatography on silica gel

Sources & evidence

ORD record
ord-ac02d1f5f07241b7b8717a6660b69a20
Source dataset
uspto-grants-2015_12
Patent number
US09224963B2

Reaction notes

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