Lithium borohydride → HCID 68766052, compound

HRID 1628430Notes

Reaction equation

HRID 1628430 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([O:8][C:9]([F:12])([F:11])[F:10])[CH:5]=[CH:4][C:3]=1[NH:13][C:14]1[N:18]([CH2:19][CH2:20][CH2:21][C:22](OCC)=[O:23])[C:17]2[C:27]([CH:32]([CH2:35][CH3:36])[CH2:33][CH3:34])=[CH:28][CH:29]=[C:30]([Cl:31])[C:16]=2[N:15]=1.[BH4-].[Li+]>O1CCCC1>[Br:1][C:2]1[CH:7]=[C:6]([O:8][C:9]([F:11])([F:10])[F:12])[CH:5]=[CH:4][C:3]=1[NH:13][C:14]1[N:18]([CH2:19][CH2:20][CH2:21][CH2:22][OH:23])[C:17]2[C:27]([CH:32]([CH2:35][CH3:36])[CH2:33][CH3:34])=[CH:28][CH:29]=[C:30]([Cl:31])[C:16]=2[N:15]=1

Participants

4

Reactant 2

HCID 4148881Lithium borohydrideHCID 68762526HCID 68762526, compound

Product 1

HCID 68766052HCID 68766052, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 4-[2-{[2-bromo-4-(trifluoromethoxy)phenyl]amino}-4-chloro-7-(1-ethylpropyl)-1H-benzimidazol-1-yl]butanoate (1.37 g, 2.32 mmol) in tetrahydrofuran (15.0 mL) was added lithium borohydride (151.5 mg, 6.96 mmol) at 0° C. The reaction mixture was stirred at room temperature for 12 hr. The reaction mixture was warmed to 60° C. and stirred for 24 hr. After cooling, the reaction mixture was quenched with water at 0° C. and extracted with ethyl acetate (×3). The combined organic layer was washed with brine, dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by silica gel column chromatography eluting with a 0-20% ethyl acetate/n-hexane gradient mixture to give the title compound as a colorless powder (558.0 mg, 1.02 mmol, 44%).

Workup

  1. temperatureThe reaction mixture was warmed to 60° C.
  2. stirringstirred for 24 hr
  3. temperatureAfter cooling
  4. customthe reaction mixture was quenched with water at 0° C.
  5. extractionextracted with ethyl acetate (×3)
  6. washThe combined organic layer was washed with brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customThe residue was purified by silica gel column chromatography
  11. washeluting with a 0-20% ethyl acetate/n-hexane gradient mixture

Sources & evidence

ORD record
ord-8e48be9b597645e8883da672b56d926a
Source dataset
uspto-grants-2014_07
Patent number
US08785460B2

Reaction notes

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