Lithium borohydride → HCID 68773966, compound

HRID 1628652Notes

Reaction equation

HRID 1628652 reaction equation
[Br:1][C:2]1[C:7]2[N:8]([CH2:20][CH2:21][CH2:22][C:23](OCC)=[O:24])[C:9]([NH:11][C:12]3[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][C:13]=3[Cl:19])=[N:10][C:6]=2[CH:5]=[CH:4][CH:3]=1.[BH4-].[Li+]>O1CCCC1>[Br:1][C:2]1[C:7]2[N:8]([CH2:20][CH2:21][CH2:22][CH2:23][OH:24])[C:9]([NH:11][C:12]3[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][C:13]=3[Cl:19])=[N:10][C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 4148881Lithium borohydrideHCID 68764903HCID 68764903, compound

Product 1

HCID 68773966HCID 68773966, compoundYield 64.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 4-{7-bromo-2-[(2,4-dichlorophenyl)amino]-1H-benzimidazol-1-yl}butanoate (Reference Example 78; 1.61 g, 3.42 mmol) in tetrahydrofuran (15 mL) was added lithium tetrahydroborate (372 mg, 17.1 mmol) at 0° C. The mixture was stirred at room temperature for 16 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 purified by flash column chromatography on silica gel eluting with a 5-30% ethyl acetate/n-hexane gradient mixture. The filtrate was concentrated in vacuo to give the crude product of 4-{7-bromo-2-[(2,4-dichlorophenyl)amino]-1H-benzimidazol-1-yl}butan-1-ol (945 mg).

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 purified by flash column chromatography on silica gel eluting with a 5-30% ethyl acetate/n-hexane gradient mixture
  9. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-834248fd44994d48930463f7e2a6e6ba
Source dataset
uspto-grants-2014_07
Patent number
US08785460B2

Reaction notes

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