HCID 178461633, compound → HCID 178458281, compound

HRID 1433204Notes

Reaction equation

HRID 1433204 reaction equation
[F:1][C:2]([F:29])([F:28])[C:3]1[CH:27]=[CH:26][C:6]([O:7][CH2:8][C:9]2[NH:13][C:12]3[CH:14]=[CH:15][C:16]([C:18]4[CH:25]=[CH:24][CH:23]=[CH:22][C:19]=4[CH:20]=[O:21])=[CH:17][C:11]=3[N:10]=2)=[CH:5][CH:4]=1.[CH2:30]([Mg]Cl)[CH3:31]>C1COCC1>[F:29][C:2]([F:1])([F:28])[C:3]1[CH:27]=[CH:26][C:6]([O:7][CH2:8][C:9]2[NH:13][C:12]3[CH:14]=[CH:15][C:16]([C:18]4[CH:25]=[CH:24][CH:23]=[CH:22][C:19]=4[CH:20]([OH:21])[CH2:30][CH3:31])=[CH:17][C:11]=3[N:10]=2)=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 178461633HCID 178461633, compoundHCID 1785194642-[2-(4-trifluoromethyl-phenoxymethyl)-1H-benzoimidazol-5-yl]-benzaldehyde

Product 1

HCID 178458281HCID 178458281, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-[2-(4-trifluoromethyl-phenoxymethyl)-1H-benzoimidazol-5-yl]-benzaldehyde (0.080 g, 0.224 mmol) in THF (6 mL) at −78° C. was added dropwise ethylmagnesium chloride (0.22 mL, 0.673 mmol, 1.0 M solution in THF). After stirring 15 min, the reaction mixture was quenched with brine. The mixture was concentrated, and the residue was purified by chromatography (silica, hexanes: EtOAc, 1:2) to afford the title compound as a off-white solid (0.084 g, 91%). 1H NMR (400 MHz, CD3OD) δ (ppm): 7.64-7.59 (m, 4H), 7.39 (td, 1H, J=8.4 Hz, J=1.6 Hz), 7.29 (td, 1H, J=8.0 Hz, J=1.2 Hz), 7.26-7.20 (m, 5H), 5.45 (s, 2H), 4.67 (t, 1H, J=6.6 Hz), 1.68-1.63 (m, 2H), 0.71 (t, 2H, J=7.6 Hz). Mass Spectrum (LCMS, ESI pos.) Calcd. For C24H22F3N2O2: 427.4 (M+H), Found 427.2.

Workup

  1. customthe reaction mixture was quenched with brine
  2. concentrationThe mixture was concentrated
  3. customthe residue was purified by chromatography (silica, hexanes: EtOAc, 1:2)

Sources & evidence

ORD record
ord-7908b1f50e1a478c829b0acf0f80fdc2
Source dataset
uspto-grants-2009_11
Patent number
US07612211B2

Reaction notes

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