Water → HCID 69849754, compound

HRID 429197Notes

Reaction equation

HRID 429197 reaction equation
[H-].[Na+].[F:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[C:18]3[C:13](=[N:14][CH:15]=[CH:16][N:17]=3)[NH:12][C:11]=2[C:19]2[CH:24]=[CH:23][N:22]=[CH:21][CH:20]=2)=[CH:6][CH:5]=1.Br[CH2:26][CH2:27][CH2:28][Cl:29].O>O1CCCC1>[Cl:29][CH2:28][CH2:27][CH2:26][N:17]1[CH2:16][CH:15]=[N:14][C:13]2[NH:12][C:11]([C:19]3[CH:24]=[CH:23][N:22]=[CH:21][CH:20]=3)=[C:10]([C:7]3[CH:8]=[CH:9][C:4]([F:3])=[CH:5][CH:6]=3)[C:18]1=2

Participants

6

Reactant 4

HCID 962WaterHCID 80061-Bromo-3-chloropropaneHCID 24758Sodium hydrideHCID 11011717HCID 11011717, compound

Product 1

HCID 69849754HCID 69849754, compoundYield 39.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
65 °C

Procedure

To a suspension of sodium hydride (1.03 g, 25.8 mmol, 60% in mineral oil) in dry tetrahydrofuran (20 ml) was slowly added 7-(4-fluorophenyl)-6-(pyridin-4-yl)-5H-pyrrolo[2,3-b]pyrazine (0.75 g, 2.58 mmol) followed by 1-bromo-3-chloropropane (4.05 g, 25.8 mmol). The reaction mixture was heated at 65° C. for 72 h. Water was added slowly to quench the excess sodium hydride and the organics were removed in vacuo. Water was added to the residue and the aqueous layer was extracted with ethyl acetate. The organic phase was washed with brine, dried over magnesium sulfate, filtered and concentrated in vacuo. The crude product was purified by flash chromatography on silica gel, elating with ethyl acetate, to give 1-(3-chloropropyl)-7-(4-fluorophenyl)-6-(pyridin-4-yl)-5H-pyrrolo[2,3-b]pyrazineas a solid (0.375 g).

Workup

  1. customto quench the excess sodium hydride
  2. customthe organics were removed in vacuo
  3. additionWater was added to the residue
  4. extractionthe aqueous layer was extracted with ethyl acetate
  5. washThe organic phase was washed with brine
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe crude product was purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-4beab2c8765846009836156d0ade7190
Source dataset
uspto-grants-2001_11
Patent number
US06316464B1

Reaction notes

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