Methyl iodide → HCID 59394352, compound

HRID 45155Notes

Reaction equation

HRID 45155 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 59394352HCID 59394352, compound

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-f0d001bda11a410ab520b0618706b3d7
Source dataset
uspto-grants-2013_09
Patent number
US08541432B2

Reaction notes

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