1-(4-fluorophenyl)-1H-indazole-5-carbaldehyde → 1-(1-(4-fluorophenyl)-1H-indazol-5-yl)-2-phenylethanol

HRID 563407Notes

Reaction equation

HRID 563407 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]3[C:11](=[CH:12][C:13]([CH:17]=[O:18])=[CH:14][CH:15]=3)[CH:10]=[N:9]2)=[CH:4][CH:3]=1.[CH2:19]([Mg]Br)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C1COCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:16]3[C:11](=[CH:12][C:13]([CH:17]([OH:18])[CH2:19][C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)=[CH:14][CH:15]=3)[CH:10]=[N:9]2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 579436121-(4-fluorophenyl)-1H-indazole-5-carbaldehydeHCID 178419663HCID 178419663, compound

Product 1

HCID 670056011-(1-(4-fluorophenyl)-1H-indazol-5-yl)-2-phenylethanolYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 1-(4-fluorophenyl)-1H-indazole-5-carbaldehyde (240 mg, 1.0 mmol) in anhydrous THF (5 mL) was added benzylmagnesium bromide (19% solution in THF, 3 mL, 3 mmol) dropwise at rt under argon. The reaction mixture was stirred at rt for 30 min and quenched by the slow addition of saturated aqueous ammonium chloride solution (5 mL). The mixture was extracted with ethyl acetate (2×4 mL). The combined ethyl acetate extracts were dried (Na2SO4), concentrated and purified by silica gel flash chromatography to give 1-(1-(4-fluorophenyl)-1H-indazol-5-yl)-2-phenylethanol (330 mg, 1.0 mmol, 100% yield) as a yellow oil.

Workup

  1. customquenched by the slow addition of saturated aqueous ammonium chloride solution (5 mL)
  2. extractionThe mixture was extracted with ethyl acetate (2×4 mL)
  3. dry with materialThe combined ethyl acetate extracts were dried (Na2SO4)
  4. concentrationconcentrated
  5. custompurified by silica gel flash chromatography

Sources & evidence

ORD record
ord-2d78b5376c9342a5a4b30540ee57d640
Source dataset
uspto-grants-2011_11
Patent number
US08067447B2

Reaction notes

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