Sodium borohydride → HCID 21075799, compound

HRID 1373951Notes

Reaction equation

HRID 1373951 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[C:6]3[N:14]([N:15]=[C:16]([CH3:18])[CH3:17])[C:13]([CH2:19][CH2:20][CH3:21])=[N:12][C:7]=3[CH:8]=[N:9][C:10]=2[CH:11]=1.[BH4-].[Na+]>CO>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[C:6]3[N:14]([NH:15][CH:16]([CH3:17])[CH3:18])[C:13]([CH2:19][CH2:20][CH3:21])=[N:12][C:7]=3[CH:8]=[N:9][C:10]=2[CH:11]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 21075800HCID 21075800, compound

Product 1

HCID 21075799HCID 21075799, compoundYield 88.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of N-(7-bromo-2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)isopropylideneamine (18.4 g, 53.3 mmol) in 100 mL of methanol was placed under an atmosphere of nitrogen and cooled in an ice water bath. The solution was treated with sodium borohydride (2.32 g, 61.3 mmol) over 30 min. The reaction mixture was allowed to slowly come to ambient temperature. After 1.5 h, the reaction was quenched by the addition of 25 mL of saturated NH4Cl solution. The reaction mixture was concentrated under reduced pressure to remove the methanol. The residue was partitioned between chloroform (150 mL) and 10% Na2CO3 solution (35 mL), and the phases were separated. The organic portion was washed with another portion of 10% Na2CO3 solution (35 mL), water (35 mL) and brine (35 mL). The organic portion was dried over Na2SO4, filtered and concentrated under reduced pressure to yield a brown foam. The foam was purified by chromatography (SiO2, 97:3 CHCl3:MeOH gradient to 9:1) to give 16.3 g of N-(7-bromo-2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)isopropylamine as a dark tan solid.

Workup

  1. temperaturecooled in an ice water bath
  2. customto slowly come to ambient temperature
  3. customthe reaction was quenched by the addition of 25 mL of saturated NH4Cl solution
  4. concentrationThe reaction mixture was concentrated under reduced pressure
  5. customto remove the methanol
  6. customThe residue was partitioned between chloroform (150 mL) and 10% Na2CO3 solution (35 mL)
  7. customthe phases were separated
  8. washThe organic portion was washed with another portion of 10% Na2CO3 solution (35 mL), water (35 mL) and brine (35 mL)
  9. dry with materialThe organic portion was dried over Na2SO4
  10. filtrationfiltered
  11. concentrationconcentrated under reduced pressure
  12. customto yield a brown foam
  13. customThe foam was purified by chromatography (SiO2, 97:3 CHCl3:MeOH gradient to 9:1)

Sources & evidence

ORD record
ord-2d6dedb274154293a4d53576cf7bf754
Source dataset
uspto-grants-2007_01
Patent number
US07163947B2

Reaction notes

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