Methyl iodide → HCID 67499544, compound

HRID 2197584Notes

Reaction equation

HRID 2197584 reaction equation
[Cl:1][C:2]1[C:3]([C:8]2([OH:18])[CH2:17][CH2:16][C:11]3([O:15][CH2:14][CH2:13][O:12]3)[CH2:10][CH2:9]2)=[N:4][CH:5]=[CH:6][CH:7]=1.[H-].[Na+].[CH3:21]I>O1CCCC1>[Cl:1][C:2]1[C:3]([C:8]2([O:18][CH3:21])[CH2:17][CH2:16][C:11]3([O:15][CH2:14][CH2:13][O:12]3)[CH2:10][CH2:9]2)=[N:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 67499969HCID 67499969, compound

Product 1

HCID 67499544HCID 67499544, compoundYield 94.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the product of Example 1A (2.16 g, 8.00 mmol) in tetrahydrofuran (70 mL) was added 60% sodium hydride (0.96 g, 24.0 mmol) in portions, followed by addition of methyl iodide (1.6 mL, 25.6 mmol). The reaction mixture was stirred at ambient temperature for 5 hours, quenched with saturated ammonium chloride (300 mL), extracted with ethyl acetate (300 mL), washed with water (300 mL), brine, dried with anhydrous sodium sulfate, filtered, and concentrated to a yellow oil. The residue was chromatographed on silica gel, eluting with 0-to-30% ethyl acetate in hexanes to provide 2.147 g (94% yield) of the title compound as a colorless oil. 1H NMR (300 MHz, DMSO-d6) δ ppm 1.59 (d, J=12.55 Hz, 2H), 1.80 (td, J=12.88, 3.73 Hz, 2H), 2.04 (td, J=13.57, 3.73 Hz, 2H), 2.23-2.32 (m, 2H), 2.92 (s, 3H), 3.87 (s, 4H), 7.37 (dd, J=7.97, 4.58 Hz, 1H), 7.88 (dd, J=7.97, 1.53 Hz, 1H), 8.51 (dd, J=4.58, 1.53 Hz, 1H). MS (DCI) m/z 284.13 (M+H)+.

Workup

  1. customquenched with saturated ammonium chloride (300 mL)
  2. extractionextracted with ethyl acetate (300 mL)
  3. washwashed with water (300 mL), brine
  4. dry with materialdried with anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated to a yellow oil
  7. customThe residue was chromatographed on silica gel
  8. washeluting with 0-to-30% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-78c9a3f59c604b94a96104953fd9337c
Source dataset
uspto-grants-2012_12
Patent number
US08338603B2

Reaction notes

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