Sodium borohydride → HCID 118452547, compound

HRID 1773237Notes

Reaction equation

HRID 1773237 reaction equation
[C:1]([C:4]1[CH:5]=[CH:6][C:7]2[O:11][C:10]([C:12]#[N:13])=[CH:9][C:8]=2[CH:14]=1)(=O)[CH3:2].[Cl:15][C:16]1[CH:17]=[C:18]([CH:20]=[CH:21][C:22]=1[CH2:23][CH2:24][CH3:25])[NH2:19].[BH4-].[Na+]>C(Cl)Cl.CC(O[Ti](OC(C)C)(OC(C)C)OC(C)C)C>[Cl:15][C:16]1[CH:17]=[C:18]([NH:19][CH:1]([C:4]2[CH:5]=[CH:6][C:7]3[O:11][C:10]([C:12]#[N:13])=[CH:9][C:8]=3[CH:14]=2)[CH3:2])[CH:20]=[CH:21][C:22]=1[CH2:23][CH2:24][CH3:25]

Participants

6

Reactant 3

HCID 4311764Sodium borohydrideHCID 13258203HCID 13258203, compoundHCID 15583087HCID 15583087, compound

Product 1

HCID 118452547HCID 118452547, compoundYield 95.3%

Reagents, catalysts & solvents 2

HCID 178460666HCID 178460666, compoundCatalystHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
50 °C

Procedure

A mixture of 5-acetylbenzofuran-2-carbonitrile (64 mg, 0.35 mmol), 3-chloro-4-propylaniline (140 mg, 0.82 mmol) and Ti(OiPr)4 (205 μL, 0.69 mmol) was heated to 50° C. for 3 hr, then 60° C. for 2 hr. The reaction mixture was diluted with 10 mL of DCM, and celite was added to the solution (enough to equal the volume of the mixture). The reaction was quenched with 5 mL of sat. NaHCO3:H2O=1:1, and filtered. The separated organic layer was washed with H2O, brine and dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue was dissolved in 1.4 mL of TFE and NaBH4 (15.69 mg, 0.415 mmol) was added. The reaction was stirred at 40° C. for 2 hr. After cooling to room temperature, the reaction mixture was diluted with 50 mL of DCM, which was then washed with H2O, brine, dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified by silica gel flash chromatography, 100% Heptane-30% Ethyl Acetate/70% Heptane, to give (±) 5-(1-((3-chloro-4-propylphenyl)amino)ethyl)benzofuran-2-carbonitrile (113 mg). LCMS retention time=1.66 minutes (LC method 1); MS (m+1)=339.3.

Workup

  1. additionwas added to the solution (enough
  2. customThe reaction was quenched with 5 mL of sat. NaHCO3
  3. filtrationH2O=1:1, and filtered
  4. washThe separated organic layer was washed with H2O, brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. additionwas added
  9. temperatureAfter cooling to room temperature
  10. washwas then washed with H2O, brine
  11. dry with materialdried over Na2SO4
  12. filtrationfiltered
  13. concentrationconcentrated under reduced pressure
  14. customThe residue was purified by silica gel flash chromatography, 100% Heptane-30% Ethyl Acetate/70% Heptane

Sources & evidence

ORD record
ord-1cf4db87aa394359b8abd11f0132f8e2
Source dataset
uspto-grants-2016_02
Patent number
US09255093B2

Reaction notes

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