1-(1H-Indol-5-yl)ethanone

To a solution of indole-5-acid (2.5 g, 15.5 mmol) in 30 mL anhydrous THF, a solution of CHTo a solution of indole-5-carboxylic acid [10G, 62.05 mmol, Intermediate (16) ] in anhydrous tetrahydrofuran (1000 mL) is added methyl lithium (1.6M in diethyl ether, 150 mL) drop wise over 60 minutes periods. The resulting precipitate is stirred at ambient temp for 40 hours. The reaction is cooled to 0°C and quenched by the cautious addition of water (5 ML) until boiling stopped. The solvent is removed in vacuo and the slurry mixture is partitioned between dichloromethane (500 ML) and water (100 mL). Dichloromethane layer is washed with 1N hydrochloric acid (20 mL), saturated NAHC03 (20 ML), brine and dried over sodium sulfate. The residue is chromatographed on 110 g silica gel cartridge (30 to 50percent ethyl acetate gradient in heptane) to afford L- (LH-INDOL-5-Y)-ETHANONE [5. 0G, 50.6percent, Intermediate (17) ] as colorless oil. Oil solidified on standing; 1H NMR (CDC13) : 8 8.846 (1H, br s), 8.356 (1H, s), 7.917 (1H, d), 7.449-7. 297 (2H, m), 6.690 (1H), 2.713 (3H, s); LC/MS : 160 (M + H).[001241j Step B: The crude product from Step A was dissolved in THF (20 mL). A 1.4 M solution of methylmagnesium bromide (11.2 mL, 15.6 mmol) in THF:toluene (3:1), was added drop wise to the solution. The solution was allowed to warm to room temperature. The solution was stirred at 50 °C for 1 hour, upon which iN aqueous HC1 (50 mL) was slowly added. The mixture was partitioned into EtOAc (200 mL) and aqueous iN NaOH (200 mL). The organic layer was washed with brine, dried over Na2504, filtered and concentrated. The residue was chromatographed on silica, eluting with EtOAc (0percent to 50percent) in hexanes to afford 1-(1H-indol-5- yl)ethanone as a white powder (323 mg, 33percent).

Molecular Weight:159.18
XLogP3:2
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:1
Exact Mass:159.068413911
Monoisotopic Mass:159.068413911
Topological Polar Surface Area:32.9
Heavy Atom Count:12
Complexity:190
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes