Methyl iodide → HCID 87782457, compound

HRID 2219818Notes

Reaction equation

HRID 2219818 reaction equation
[OH:1]/[N:2]=[C:3](/[C:8]1[CH:13]=[CH:12][C:11]([C:14]2[N:18]([CH3:19])[C:17]([C:20]#[N:21])=[CH:16][CH:15]=2)=[CH:10][CH:9]=1)\[C:4]([CH3:7])([CH3:6])[CH3:5].[H-].[Na+].[CH3:24]I>C1COCC1>[CH3:24][O:1]/[N:2]=[C:3](/[C:8]1[CH:13]=[CH:12][C:11]([C:14]2[N:18]([CH3:19])[C:17]([C:20]#[N:21])=[CH:16][CH:15]=2)=[CH:10][CH:9]=1)\[C:4]([CH3:7])([CH3:6])[CH3:5]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 46919612HCID 46919612, compound

Product 1

HCID 87782457HCID 87782457, compoundYield 10.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 5-{4-[(1E)-N-hydroxy-2,2-dimethylpropanimidoyl]-phenyl}-1-methyl-1H-pyrrole-2-carbonitrile (0.212 g, 0.75 mmol) in THF (7 mL) was added sodium hydride (0.03 g, 60% in mineral oil, 0.75 mmol) at 0° C. After the mixture was stirred for 10 minutes, methyl iodide (0.8 mL, 1.28 mmol) was added and the resulting mixture was stirred overnight at room temperature. The reaction mixture was then quenched with a saturated ammonium chloride solution (20 mL), and extracted several times with ethyl acetate (3×20 mL). The combined organic layers were dried over magnesium sulfate and concentrated. The residue was purified by a silica gel column (5% ethyl acetate in hexane) to afford 5-{4-[(1E)-N-methoxy-2,2-dimethylpropanimidoyl]phenyl}-1-methyl-1H-pyrrole-2-carbonitrile as a white solid (0.023 g, 10%). MS (ES) m/z 296.0; HRMS: calcd for C18H21N3O+H+, 296.17574; found (ESI, [M+H]+), 296.1753.

Workup

  1. stirringthe resulting mixture was stirred overnight at room temperature
  2. customThe reaction mixture was then quenched with a saturated ammonium chloride solution (20 mL)
  3. extractionextracted several times with ethyl acetate (3×20 mL)
  4. dry with materialThe combined organic layers were dried over magnesium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by a silica gel column (5% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-87b376b1be8043e9b762986be0dec48a
Source dataset
uspto-grants-2008_08
Patent number
US07414142B2

Reaction notes

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