Sodium borohydride → HCID 178521386, compound

HRID 1433217Notes

Reaction equation

HRID 1433217 reaction equation
[OH:1][CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C:11]1[CH:31]=[CH:30][C:14]2[NH:15][C:16]([CH2:18][O:19][C:20]3[CH:25]=[CH:24][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:22][CH:21]=3)=[N:17][C:13]=2[CH:12]=1)=[O:4].[BH4-].[Na+]>C(O)C>[F:29][C:26]([F:27])([F:28])[C:23]1[CH:24]=[CH:25][C:20]([O:19][CH2:18][C:16]2[NH:15][C:14]3[CH:30]=[CH:31][C:11]([C:6]4[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=4[CH:3]([OH:4])[CH2:2][OH:1])=[CH:12][C:13]=3[N:17]=2)=[CH:21][CH:22]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 1785213852-hydroxy-1-{2-[2-(4-trifluoromethyl-phenoxymethyl)-1H-benzoimidazol-5-yl]-phenyl}-ethanone

Product 1

HCID 178521386HCID 178521386, compoundYield 91.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 2-hydroxy-1-{2-[2-(4-trifluoromethyl-phenoxymethyl)-1H-benzoimidazol-5-yl]-phenyl}-ethanone (0.082 g, 0.192 mmol) in ethanol (6 mL) was added sodium borohydride (0.029 g, 0.769 mmol) at 0° C. After stirring for 20 min, the reaction was quenched by water. EtOAc was added to dilute and the organic layer was washed with brine, dried over Na2SO4, and concentrated under reduced pressure to provide a residue, which was purified by chromatography (silica, CH2Cl2: MeOH, 10:1) to afford the title compound as a pale yellow oil (0.075 g, 91%). 1H NMR (400 MHz, CD3OD) δ (ppm): 7.64-7.61 (m, 4H), 7.40 (dt, 1H, J=8.4 Hz, J=1.6 Hz), 7.32 (dt, 1H, J=8.2 Hz, J=1.6 Hz), 7.26-7.23 (m, 5H), 5.45 (s, 2H), 4.86 (dd, 1H, J=6.8 Hz, J=1.2 Hz), 3.58-3.55 (m, 1H), 1.60-1.57 (m, 1H). Mass Spectrum (LCMS, ESI pos.) Calcd. For C23H20F3N2O3: 429.4 (M+H), Found 429.1.

Workup

  1. customthe reaction was quenched by water
  2. additionEtOAc was added
  3. additionto dilute
  4. washthe organic layer was washed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated under reduced pressure
  7. customto provide a residue, which
  8. customwas purified by chromatography (silica, CH2Cl2: MeOH, 10:1)

Sources & evidence

ORD record
ord-35a4e574166343bc89e458bf96d7f3c7
Source dataset
uspto-grants-2009_11
Patent number
US07612211B2

Reaction notes

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