Diethyl Ether → HCID 21713650, compound

HRID 649804Notes

Reaction equation

HRID 649804 reaction equation
[H-].[Na+].[O:3]=[C:4]1[NH:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[N:6]=[C:5]1[C:14]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[N:16]([CH2:23][CH2:24][CH2:25][N:26]2[C:34](=[O:35])[C:33]3C(=CC=CC=3)C2=O)[CH:15]=1.CI.[CH2:39]([O:41]CC)C>CN(C)C=O>[C:34]([O-:35])(=[O:41])[CH3:33].[CH3:39][N:13]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[N:6]=[C:5]([C:14]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[N:16]([CH2:23][CH2:24][CH2:25][NH3+:26])[CH:15]=2)[C:4]1=[O:3]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 21713654HCID 21713654, compound

Product 1

HCID 21713650HCID 21713650, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
-20 °C

Procedure

A dispersion of sodium hydride, 55-60% in oil, (0.0075 g, 0.17 mmol) in dry dimethyl formamide (2 ml) was cooled to −20° C. A solution 2-{3-[3-(3-oxo-3,4-dihydro-quinoxalin-2-yl)-indol-1-yl]-propyl}-isoindol-1,3-dione (0.050 g, 0.11 mmol) in dry dimethyl formamide (2 ml), was added dropwise and the resulting mixture kept at −20° C. for 5 min and then at room temperature for another 15 min. The reaction mixture was cooled to −20° C and methyl iodide (0.017 g, 0.12 mmol, 7.7 μl) was added via a syringe. The resulting solution was allowed to reach room temperature whereupon 12 ml of diethyl ether was added. After 2 h at room temperature, 2-{3-[3-(4-methyl-3-oxo-3,4-dihydro-quinoxalin-2-yl)-indol-1-yl]-propyl}-isoindole-1,3-dione was precipitated.

Workup

  1. waitat room temperature for another 15 min
  2. additionwas added
  3. waitAfter 2 h at room temperature
  4. custom2-{3-[3-(4-methyl-3-oxo-3,4-dihydro-quinoxalin-2-yl)-indol-1-yl]-propyl}-isoindole-1,3-dione was precipitated

Sources & evidence

ORD record
ord-3cd66cf909e0455e8970fceb1aa67b35
Source dataset
uspto-grants-2001_08
Patent number
US06271231B1

Reaction notes

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