Allyl bromide → HCID 18999808, compound

HRID 2260115Notes

Reaction equation

HRID 2260115 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].[CH2:23]1[CH2:27]OC[CH2:24]1.[H-].[Na+].[CH2:30](Br)[CH:31]=[CH2:32]>O>[CH2:27]([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)[CH:23]=[CH2:24].[CH2:32]([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)[CH:31]=[CH2:30]

Participants

7

Reactant 4

HCID 7841Allyl bromideHCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 9860908HCID 9860908, compound

Product 2

HCID 18999808HCID 18999808, compoundHCID 18999910HCID 18999910, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

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. It is stirred at room temperature for 10 minutes, then allyl bromide 0.206 g is added dropwise into the red mixture. The resulting mixture is stirred at room temperature overnight then poured into water, extracted with methylene chloride and the organic layer is separated, dried (Na2SO4), concentrated in vacuo which gives yellow crude product. This is purified by silica-gel column chromatography using methylene chloride, then changed to 1%-4% acetone/methylene chloride as the solvent system to obtain 1-allyl-7-(3-fluoro-4-methoxyphenyl)-1H-pyrazolo[3,4-g]quinoxaline (m.p. 121°-124° C.) and 2-allyl-7-(3-fluoro-4-methoxy-phenyl)-2H-pyrazolo[3,4-g]quinoxaline (m.p. 196°-200° C.).

Workup

  1. stirringThe resulting mixture is stirred at room temperature overnight
  2. extractionextracted with methylene chloride
  3. customthe organic layer is separated
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated in vacuo which
  6. customgives yellow crude product
  7. customThis is purified by silica-gel column chromatography

Sources & evidence

ORD record
ord-3c214d7e5bd647b0a0f6f3fba56c3b73
Source dataset
uspto-grants-1995_12
Patent number
US05476851

Reaction notes

Loading…