Benzyl Bromide → HCID 11639750, compound

HRID 1619478Notes

Reaction equation

HRID 1619478 reaction equation
[CH:1]1[C:13]2[NH:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[C:3]([C:14]([OH:16])=[O:15])[N:2]=1.[H-].[Na+].[CH2:19](Br)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C([O-])(O)=O.[Na+]>O.C(OCC)(=O)C.CN(C=O)C>[CH2:19]([N:12]1[C:13]2[CH:1]=[N:2][C:3]([C:14]([O:16][CH2:5][C:6]3[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=3)=[O:15])=[CH:4][C:5]=2[C:6]2[C:11]1=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

8

Reactant 4

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 1732629H-Pyrido(3,4-b)indole-3-carboxylic acidHCID 516892Sodium Bicarbonate

Product 1

HCID 11639750HCID 11639750, compoundYield 57%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Compound 17 (2.12 g, 10 mmol) was mixed with DMF (50 ml). After stirring the mixture at room temperature for 30 minutes, NaH (1.6 g, 40 mmol) was added and stirred until the solution became clear. After that, benzyl bromide (5 ml) was added. The mixture was stirred and reacted at room temperature for 1 h. The reaction mixture was poured into cold water (200 ml) and the mixture was extracted with ethyl acetate. The organic phases were combined and washed with water and brine, then the organic phase was evaporated in reduced pressure, the residue was dissolved in anhydrous ethanol, and then the mixture was adjusted to pH 4 with concentrated HCl, and evaporated and recrystallized with acetone/ethyl ether, light yellow solids were obtained. The light yellow solids were dissolved in a mixed solution of water and ethyl acetate. The pH was adjusted to 8 with saturated NaHCO3 solution. The organic phases were isolated. The aqueous layer was extracted with ethyl acetate. After drying, decolorization with activated carbon, filtration, concentration, and recrystallization with ethyl ether, white solids (2.3 g, 57%) were obtained, mp 169-170° C.

Workup

  1. stirringstirred until the solution
  2. stirringThe mixture was stirred
  3. customreacted at room temperature for 1 h
  4. extractionthe mixture was extracted with ethyl acetate
  5. washwashed with water and brine
  6. customthe organic phase was evaporated in reduced pressure
  7. dissolutionthe residue was dissolved in anhydrous ethanol
  8. customevaporated
  9. customrecrystallized with acetone/ethyl ether
  10. customlight yellow solids were obtained
  11. customThe organic phases were isolated
  12. extractionThe aqueous layer was extracted with ethyl acetate
  13. customAfter drying
  14. filtrationdecolorization with activated carbon, filtration, concentration, and recrystallization with ethyl ether

Sources & evidence

ORD record
ord-b88fb4a8225a4237adaf1daf05d4c534
Source dataset
uspto-grants-2014_07
Patent number
US08772311B2

Reaction notes

Loading…