Lithium borohydride → HCID 68761693, compound

HRID 1628425Notes

Reaction equation

HRID 1628425 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10]1[N:14]([CH2:15][CH2:16][CH2:17][C:18](OCC)=[O:19])[C:13]2[C:23]([CH:28]([CH2:31][CH3:32])[CH2:29][CH3:30])=[CH:24][CH:25]=[C:26]([Cl:27])[C:12]=2[N:11]=1.[BH4-].[Li+]>O1CCCC1>[Br:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10]1[N:14]([CH2:15][CH2:16][CH2:17][CH2:18][OH:19])[C:13]2[C:23]([CH:28]([CH2:31][CH3:32])[CH2:29][CH3:30])=[CH:24][CH:25]=[C:26]([Cl:27])[C:12]=2[N:11]=1

Participants

4

Reactant 2

HCID 4148881Lithium borohydrideHCID 68764242HCID 68764242, compound

Product 1

HCID 68761693HCID 68761693, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 4-[2-[(2-bromo-4-methylphenyl)amino]-4-chloro-7-(1-ethylpropyl)-1H-benzimidazol-1-yl]butanoate (1.42 g, 2.74 mmol) in tetrahydrofuran (15.0 mL) was added lithium borohydride (178.7 mg, 8.20 mmol) at 0° C. The reaction mixture was stirred at room temperature for 24 hr. The reaction mixture was quenched with water at 0° C. and extracted with ethyl acetate (×3). The combined organic layer was washed with brine (×1), dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo. The resulting solid was suspended n-hexane and stirred at 70° C. for 30 min. After cooling, the solid was collected by filtration to give the title compound as a colorless powder (1.03 g, 2.16 mmol, 79%).

Workup

  1. customThe reaction mixture was quenched with water at 0° C.
  2. extractionextracted with ethyl acetate (×3)
  3. washThe combined organic layer was washed with brine (×1)
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. stirringstirred at 70° C. for 30 min
  8. temperatureAfter cooling
  9. filtrationthe solid was collected by filtration

Sources & evidence

ORD record
ord-fd0b10e38f3148278764e72e67220e2e
Source dataset
uspto-grants-2014_07
Patent number
US08785460B2

Reaction notes

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