1-(1H-indazol-6-yl)ethanol synthesis

Yield:181820-44-0 60%

Reaction Conditions:

in tetrahydrofuran at -78 - 20;

Steps:

A51.A

To a solution of lH-indazole-6-carbaldehyde (200 mg, 1.37 mmol) in THF (7 mL) at -78⁰C 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 x 10 mL), dried over MgSO₄ and concentrated. The yellow oil was purified by silica gel chromatography (EtO Ac/Hex 4:1) to yield the title compound as a clear oil (135 mg, 60%). ¹H NMR (400 MHz, CDCl₃) δ 8.07 (s, IH), 7.76 (s, IH), 7.50-7.47 (m, 2H), 5.05 (q, 1 H, 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.

References:

WO2009/79767,2009,A1 Location in patent:Page/Page column 127