Methyl iodide → HCID 86673029, compound

HRID 1853262Notes

Reaction equation

HRID 1853262 reaction equation
[C:1]([O:5][N:6]=[C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[O:10][C:9]([C:17]2[N:18]=[CH:19][C:20]3[C:25]([CH:26]=2)=[C:24]([OH:27])[CH:23]=[CH:22][CH:21]=3)=[CH:8]1)([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].I[CH3:31]>CN(C)C=O.[Cl-].[Na+].O>[C:1]([O:5][N:6]=[C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[O:10][C:9]([C:17]2[N:18]=[CH:19][C:20]3[C:25]([CH:26]=2)=[C:24]([O:27][CH3:31])[CH:23]=[CH:22][CH:21]=3)=[CH:8]1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 136352221HCID 136352221, compound

Product 1

HCID 86673029HCID 86673029, compoundYield 79%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a ice-water bath cooled solution of 2-(5-hydroxy-isoquinolin-3-yl)-chromen-4-one O-tert-butyl oxime (80 mg, 0.22 mmol) in dimethylformamide (2.5 ml) was added sodium hydride (60% in mineral oil, 13 mg, 0.33 mmol) under argon and the mixture was stirred at room temperature for 1 hour. The solution was cooled to 0° C. and iodomethane (15 μl, 0.24 mmol) was added. The resulting solution was stirred at room temperature for 20 hours and then hydrolyzed with brine. The mixture was extracted with ethyl acetate, washed with brine, dried over sodium sulfate and then purified by flash chromatography over silica gel (cyclohexane/ethyl acetate: 80/20) to yield 2-(5-methoxy-isoquinolin-3-yl)-chromen-4-one O-tert-butyl oxime (65 mg, 79%) as a yellow solid.

Workup

  1. temperatureThe solution was cooled to 0° C.
  2. stirringThe resulting solution was stirred at room temperature for 20 hours
  3. extractionThe mixture was extracted with ethyl acetate
  4. washwashed with brine
  5. dry with materialdried over sodium sulfate
  6. custompurified by flash chromatography over silica gel (cyclohexane/ethyl acetate: 80/20)

Sources & evidence

ORD record
ord-23a9c45d7b9744d8b8f0e2b3ae7403e4
Source dataset
uspto-grants-2015_02
Patent number
US08962627B2

Reaction notes

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