Benzyl iodide → HCID 18999856, compound

HRID 2260116Notes

Reaction equation

HRID 2260116 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:10]2[CH:11]=[N:12][C:13]3[CH:14]=[C:15]4[CH:22]=[N:21][NH:20][C:16]4=[CH:17][C:18]=3[N:19]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].[H-].[Na+].[CH2:25](I)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>C1COCC1>[CH2:25]([N:20]1[C:16]2=[CH:17][C:18]3[N:19]=[C:10]([C:4]4[CH:5]=[CH:6][C:7]([O:8][CH3:9])=[C:2]([F:1])[CH:3]=4)[CH:11]=[N:12][C:13]=3[CH:14]=[C:15]2[CH:22]=[N:21]1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.[CH2:25]([N:21]1[CH:22]=[C:15]2[C:16]([CH:17]=[C:18]3[C:13](=[CH:14]2)[N:12]=[CH:11][C:10]([C:4]2[CH:5]=[CH:6][C:7]([O:8][CH3:9])=[C:2]([F:1])[CH:3]=2)=[N:19]3)=[N:20]1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

6

Reactant 3

HCID 12098Benzyl iodideHCID 24758Sodium hydrideHCID 9860908HCID 9860908, compound

Product 2

HCID 18999856HCID 18999856, compoundHCID 18999875HCID 18999875, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 0.50 g of 7-(3-fluoro-4-methoxyphenyl)-1H-pyrazolo[3,4-g]quinoxaline, 30 ml of anhydrous THF is added 0.061 g of 60% NaH. The red-orange mixture is stirred at room temperature for 10 minutes, then 0.265 g of benzyl iodide is added and is stirred at room temperature overnight. The mixture is filtered, washed with CH2Cl2. The filtrate and the CH2Cl2 wash are combined and mixed with water, extracted with CH2Cl2, separated, dried (Na2SO4) and concentrated in vacuo to give yellow crude solid. This is purified by silica-gel column chromatography using the combination of ethylacetate: hexane: methylene chloride as solvent to obtain 1-benzyl-7-(3-fluoro-4-methoxyphenyl)-1H-pyrazolo[3,4-g]quinoxaline (m.p. 149°-155° C.) and 2-benzyl-7-(3-fluoro-4-methoxyphenyl)-2H-pyrazolo[3,4-g]quinoxaline (m.p. 225°-227° C.).

Workup

  1. stirringis stirred at room temperature overnight
  2. filtrationThe mixture is filtered
  3. washwashed with CH2Cl2
  4. washThe filtrate and the CH2Cl2 wash
  5. additionmixed with water
  6. extractionextracted with CH2Cl2
  7. customseparated
  8. dry with materialdried (Na2SO4)
  9. concentrationconcentrated in vacuo
  10. customto give yellow crude solid
  11. customThis is purified by silica-gel column chromatography

Sources & evidence

ORD record
ord-3e60bed52f0b453a87506679c8787f3b
Source dataset
uspto-grants-1995_12
Patent number
US05476851

Reaction notes

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