7-Benzyloxyindole

Pale-Yellow Solid

A mixture of Intermediate 30 (31.8 g, 130 mmol), pyrrolidine (11.0 mL, 130 mmol), and N, N-dimethylformamide dimethyl acetal (52 mL, 392 mmol) in anhydrous N, N-dimethylformamide (100 mL) was heated at 110° C. under a nitrogen blanket for 3 hours. The cooled mixture was diluted with water (1.5 L), extracted with ether (2.x.500 mL), dried over Na2SO4, and filtered. The solvent was removed under reduced pressure to afford the intermediate enamine as a dark red oil, which was immediately used in the next step without purification. [0238] A solution of the enamine fin methanol (150 mL) and acetic acid (5 mL) was treated with a catalytic amount of 10percent palladium on carbon (2 g, 10percent wet), and the resulting mixture was stirred under a hydrogen atmosphere (50 psi) at room temperature for 2 hours. The palladium catalyst was removed by vacuum filtration through MgSO4 (10 g), and the filtrate was concentrated under reduced pressure to provide a dark brown residue. The residue was purified by flash column chromatography, eluting with ethyl acetate/chloroform (1:19), to provide Intermediate 31 as an off-white solid (3.82 g, 21percent over three steps): TLC Rf (4:1 hexanes/ethyl acetate)=0.61; 1H NMR (300 MHz, DMSO-d6): δ 11.18 (s, 1H), 7.56 (d, J=7.2 Hz, 2H), 7.43-7.38 (m, 3H), 7.35 (s, 1H), 7.23 (d, J=2.9 Hz, 1H), 6.88 (t, J=7.6 Hz, 1H), 6.72 (d, J=7.6 Hz, 1H), 6.39 (t, J=2.5 Hz, 1H), 2-5.26 (s, 2H) ppm.

Indole analogue as inhibitor

Molecular Weight:223.27
XLogP3:3.5
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:3
Exact Mass:223.099714038
Monoisotopic Mass:223.099714038
Topological Polar Surface Area:25
Heavy Atom Count:17
Complexity:237
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes