Lithium borohydride → HCID 68765623, compound

HRID 1628432Notes

Reaction equation

HRID 1628432 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[N:13]([CH2:14][CH2:15][CH2:16][C:17](OCC)=[O:18])[C:12]3[C:22]([CH:27]([CH2:30][CH3:31])[CH2:28][CH3:29])=[CH:23][CH:24]=[C:25]([Cl:26])[C:11]=3[N:10]=2)=[C:4]([CH3:32])[CH:3]=1.[BH4-].[Li+]>O1CCCC1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[N:13]([CH2:14][CH2:15][CH2:16][CH2:17][OH:18])[C:12]3[C:22]([CH:27]([CH2:30][CH3:31])[CH2:28][CH3:29])=[CH:23][CH:24]=[C:25]([Cl:26])[C:11]=3[N:10]=2)=[C:4]([CH3:32])[CH:3]=1

Participants

4

Reactant 2

HCID 4148881Lithium borohydrideHCID 68763229Ethyl 4-[2-[(4-bromo-2-methylphenyl)amino]-4-chloro-7-(1-ethylpropyl)-1H-benzimidazol-1-yl]butanoate

Product 1

HCID 68765623HCID 68765623, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 4-[2-[(4-bromo-2-methylphenyl)amino]-4-chloro-7-(1-ethylpropyl)-1H-benzimidazol-1-yl]butanoate (2.07 g, 3.97 mmol) in tetrahydrofuran (40 mL) was added lithium tetrahydroborate (260 mg, 11.9 mmol) at 0° C. The mixture was stirred at room temperature for 19 hr, and the reaction was quenched by methanol. The mixture was concentrated in vacuo, neutralized with aqueous saturated ammonium chloride, and extracted with ethyl acetate. The combined organic layer was washed with brine, dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo. The residue was recrystallized from ethyl acetate to give the title compound as a colorless crystal (1.10 g, 2.30 mmol, 58%).

Workup

  1. customthe reaction was quenched by methanol
  2. concentrationThe mixture was concentrated in vacuo
  3. extractionextracted with ethyl acetate
  4. washThe combined organic layer was washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-07ee466a45b047719bcaba34309ffa5a
Source dataset
uspto-grants-2014_07
Patent number
US08785460B2

Reaction notes

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