Methyl iodide → HCID 72258472, compound

HRID 12560Notes

Reaction equation

HRID 12560 reaction equation
[H-].[Na+].[C:3]1([C:9]2[CH:10]=[CH:11][C:12]([C:21](=[N:23][OH:24])[CH3:22])=[N:13][C:14]=2[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH3:25]I>C1COCC1>[CH3:25][O:24][N:23]=[C:21]([C:12]1[CH:11]=[CH:10][C:9]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=2)=[C:14]([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[N:13]=1)[CH3:22]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 1363865231-(5,6-Diphenyl-pyridin-2-yl)-ethanone Oxime2×

Product 1

HCID 72258472HCID 72258472, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

General Procedure Q. To a suspension of NaH (20 mg, 0.80 mmol) in THF (2 ml) at 0° C. was added a solution of 1-(5,6-diphenyl-pyridin-2-yl)-ethanone oxime (Compound 80, 46 mg, 0.16 mmol) in THF (1 ml). After the mixture was stirred at the same temperature for 1 hour, MeI (140 mg, 0.99 mmol) was added and the solution was stirred overnight at room temperature. The reaction was quenched with water, and the products were extracted with ethyl acetate. The combined organic layers were washed with brine and dried over Na2SO4. The filtered solvent was concentrated in vacuo, and the residue was purified by silica gel chromatography (10% ethyl acetate in hexane) to give title compound as an oil.

Workup

  1. stirringthe solution was stirred overnight at room temperature
  2. customThe reaction was quenched with water
  3. extractionthe products were extracted with ethyl acetate
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationThe filtered solvent was concentrated in vacuo
  7. customthe residue was purified by silica gel chromatography (10% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-ac7e8f852d0443e7b1a6cf595f6c716d
Source dataset
uspto-grants-2010_06
Patent number
US07728014B2

Reaction notes

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