Methyl iodide → HCID 86673057, compound

HRID 1853288Notes

Reaction equation

HRID 1853288 reaction equation
[C:1]([O:5][N:6]=[C:7]1[C:16]2[C:11](=[CH:12][C:13]([C:17]#[C:18][C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([NH2:25])[CH:20]=3)=[CH:14][CH:15]=2)[O:10][C:9]([C:26]2[N:27]=[CH:28][C:29]3[C:34]([CH:35]=2)=[CH:33][CH:32]=[CH:31][CH:30]=3)=[CH:8]1)([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].I[CH3:39]>CN(C)C=O>[C:1]([O:5][N:6]=[C:7]1[C:16]2[C:11](=[CH:12][C:13]([C:17]#[C:18][C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([NH:25][CH3:39])[CH:20]=3)=[CH:14][CH:15]=2)[O:10][C:9]([C:26]2[N:27]=[CH:28][C:29]3[C:34]([CH:35]=2)=[CH:33][CH:32]=[CH:31][CH:30]=3)=[CH:8]1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 86673058HCID 86673058, compound

Product 1

HCID 86673057HCID 86673057, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 7-(3-aminophenylethynyl)-2-(Isoquinolin-3-yl)-chromen-4-one O-tert-butyl oxime (tert-butyl protected oxime of example 29) (127 mg, 0.286 mmol) in dimethylformamide (3 ml) was added to a cold suspension of sodium hydride (60% in mineral oil, 24 mg, 0.608 mmol) in DMF (1 ml). The reaction mixture was stirred for 1 hour at room temperature and cooled to 0° C. Iodomethane (43 μl, 0.690 mmol) was added and the solution was stirred at room temperature for 18 hours. The mixture was poured onto water and extracted with ethyl acetate. The organic extracts were washed with water, brine, dried over sodium sulfate and absorbed over silica gel for purification by flash chromatography (gradient cyclohexane/dichloromethane: 0-45%) to yield 2-Isoquinolin-3-yl-7-{3-methylaminophenylethynyl}-chromen-4-one O-tert-butyl oxime (65 mg, 50%) as a beige solid.

Workup

  1. temperaturecooled to 0° C
  2. stirringthe solution was stirred at room temperature for 18 hours
  3. additionThe mixture was poured onto water
  4. extractionextracted with ethyl acetate
  5. washThe organic extracts were washed with water, brine
  6. dry with materialdried over sodium sulfate
  7. customabsorbed over silica gel for purification by flash chromatography (gradient cyclohexane/dichloromethane: 0-45%)

Sources & evidence

ORD record
ord-ffbf1ae415ce4eee9dbae0f544c8edd0
Source dataset
uspto-grants-2015_02
Patent number
US08962627B2

Reaction notes

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