1-ethyl-1H-indole-6-carbaldehyde synthesis

Yield:854778-47-5 196 mg

Reaction Conditions:

Stage #1: 1H-indole-6-carbaldehydewith potassium-t-butoxide in tetrahydrofuran at 20; for 0.333333 h;
Stage #2: ethyl iodide in tetrahydrofuran; for 1 h;

Steps:

9.A A) l-ethyl-lH-indole-6-carbaldehyde

[0405] Potassium tert-butoxide (170 mg) was added to a solution of lH-indole-6-carbaldehyde (200 mg) in THF (10 mL), the resultant was stirred for 20 minutes at room temperature, and iodoethane (236 mg) was added thereto, and the resultant was further stirred for 1 hour. The reaction mixture was diluted by ethyl acetate, the resultant was sequentially washed with water and a saturated saline solution. After the obtained organic layer was dried over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure. The obtained residue was purified by a silica gel column chromatography (hexane/ethyl acetate), thereby obtaining the title compound (196 mg). 1H MR (400 MHz, DMSO-dg) δ 1.41 (3H, t, J = 7.2 Hz), 4.33 (2H, q, J = 7.2 Hz), 6.58 (1H, d, J = 3.0 Hz), 7.56 (1H, d, J = 8.3 Hz), 7.66-7.79 (2H, m), 8.13 (1H, s), 10.02 (1H, s).

References:

WO2014/142363,2014,A1 Location in patent:Paragraph 0405