Methyl iodide → HCID 22573170, compound

HRID 567738Notes

Reaction equation

HRID 567738 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[C:8]([O:15][C@H:16]1[CH2:21][CH2:20][C@H:19]([OH:22])[CH2:18][CH2:17]1)[CH:7]=[N:6]2.[H-].[Na+].[CH3:25]I>C1COCC1.CN(C=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[C:8]([O:15][CH:16]1[CH2:21][CH2:20][CH:19]([O:22][CH3:25])[CH2:18][CH2:17]1)[CH:7]=[N:6]2

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 178486825HCID 178486825, compound

Product 1

HCID 22573170HCID 22573170, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 21974620tetrahydrofuran N,N-dimethylformamideSolvent

Procedure

A mixture of cis/trans-4-(6,7-dimethoxy-quinoxalin-2-yloxy)-cyclohexanol (170 mg, 0.56 mmole) and NaH (60%, 22.4 mg, 0.56 mmole) in anhydrous THF/DMF (10 mL/2 mL) is stirred at 0° C. for 10 min. before addition of methyl iodide (50 μL, 0.56 mmole). After being stirred at ROOM TEMPERATURE for four hours, the reaction is quenched with water (0.5 mL) and concentrated. The aqueous layer is extracted with methylene chloride (2×20 mL) and the combined organic solutions are washed with brine (5 mL). The residue after concentration is chromatographed on silica gel (30% ethyl acetate/hexane) to give 80 mg (45%) of the desired product (m.p. 85-90° C.).

Workup

  1. customthe reaction is quenched with water (0.5 mL)
  2. concentrationconcentrated
  3. extractionThe aqueous layer is extracted with methylene chloride (2×20 mL)
  4. washthe combined organic solutions are washed with brine (5 mL)
  5. concentrationThe residue after concentration
  6. customis chromatographed on silica gel (30% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-e64f602f7a4848cd95c028599e3f4c7e
Source dataset
uspto-grants-2001_01
Patent number
US06180632B2

Reaction notes

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