Methyl iodide → 3-(2,5-Dimethyl-pyrrol-1-yl)-1-methyl-5-(2,2,2-trifluoro-1-methoxy-1-methyl-ethyl)-1H-pyrazole

HRID 1887650Notes

Reaction equation

HRID 1887650 reaction equation
[CH3:1][C:2]1[N:3]([C:8]2[CH:9]=[C:10]([C:14]([OH:20])([CH3:19])[C:15]([F:18])([F:17])[F:16])[N:11]([CH3:13])[N:12]=2)[C:4]([CH3:7])=[CH:5][CH:6]=1.[H-].[Na+].[CH3:23]I>C1COCC1>[CH3:7][C:4]1[N:3]([C:8]2[CH:9]=[C:10]([C:14]([O:20][CH3:23])([CH3:19])[C:15]([F:18])([F:17])[F:16])[N:11]([CH3:13])[N:12]=2)[C:2]([CH3:1])=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 593945082-[5-(2,5-Dimethyl-pyrrol-1-yl)-2-methyl-2H-pyrazol-3-yl]-1,1,1-trifluoro-propan-2-ol

Product 1

HCID 593943523-(2,5-Dimethyl-pyrrol-1-yl)-1-methyl-5-(2,2,2-trifluoro-1-methoxy-1-methyl-ethyl)-1H-pyrazole

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-[5-(2,5-dimethyl-pyrrol-1-yl)-2-methyl-2H-pyrazol-3-yl]-1,1,1-trifluoro-propan-2-ol (0.5 g, 1.7 mmol) in THF (10 mL) at 0° C., sodium hydride (0.21 g, 60%, 5.2 mmol) is added, and the mixture is stirred for 10 min followed by the addition of methyl iodide (0.22 mL, 3.5 mmol). The ice bath is removed and the reaction mixture is stirred at room temperature for 5 hour, poured into water, separated, and the water layer is extracted with DCM. The organic layers are combined and concentrated. The residue is purified by FCC to give the title compound. MS (ESI) m/z 302.0 (M+1).

Workup

  1. customThe ice bath is removed
  2. stirringthe reaction mixture is stirred at room temperature for 5 hour
  3. additionpoured into water
  4. customseparated
  5. extractionthe water layer is extracted with DCM
  6. concentrationconcentrated
  7. customThe residue is purified by FCC

Sources & evidence

ORD record
ord-edc1a86c3078460088e4c615e297251e
Source dataset
uspto-grants-2013_08
Patent number
US08501756B2

Reaction notes

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