1H-Indazole-6-carbaldehyde → 1-(1H-Indazol-6-yl)ethanol

HRID 1615257Notes

Reaction equation

HRID 1615257 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([CH:10]=[O:11])[CH:8]=2)[CH:3]=[N:2]1.[CH3:12][Mg]Br>C1COCC1>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([CH:10]([OH:11])[CH3:12])[CH:8]=2)[CH:3]=[N:2]1

Participants

4

Reactant 2

HCID 185383681H-Indazole-6-carbaldehydeHCID 178418573HCID 178418573, compound

Product 1

HCID 687611451-(1H-Indazol-6-yl)ethanolYield 60.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1H-indazole-6-carbaldehyde (200 mg, 1.37 mmol) in THF (7 mL) at −78° C. was added methyl magnesium bromide (1.4 mL, 4.11 mmol) dropwise under argon. The solution was warmed to rt and quenched with saturated ammonium chloride (2 mL). The mixture was extracted into ethyl acetate (3×10 mL), dried over MgSO4 and concentrated. The yellow oil was purified by silica gel chromatography (EtOAc/Hex 4:1) to yield the title compound as a clear oil (135 mg, 60%). 1H NMR (400 MHz, CDCl3) δ 8.07 (s, 1H), 7.76 (s, 1H), 7.50-7.47 (m, 2H), 5.05 (q, 1H, J=7.4 Hz), 1.57 (d, 3H, J=7.2 Hz); MS ESI [M+H]+, calcd for [C9H10N2O+H]+ 163.1; found m/z 163.0.

Workup

  1. customquenched with saturated ammonium chloride (2 mL)
  2. extractionThe mixture was extracted into ethyl acetate (3×10 mL)
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. customThe yellow oil was purified by silica gel chromatography (EtOAc/Hex 4:1)

Sources & evidence

ORD record
ord-e42229c745e2446bafb7cca923dee6ad
Source dataset
uspto-grants-2014_07
Patent number
US08765748B2

Reaction notes

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