1-(PHENYLSULFONYL)-1H-INDOLE-3-CARBALDEHYDE

NaH (60percent dispersion in mineral oil, 40.00 mmol, 0.96 g) was added portionwise to a stirred solution of indole-3-carboxaldehyde 11 (20.00 mmol, 2.90 g) in anhydrous THF (50 mL) cooled in an ice bath, then slowly allowed to warm to r.t. After stirring for 30 min PhSOTo a solution of indole 3-carboxaldehyde (8y) (100 mmol) in ethanol (500 mL) at RT was added potassium hydroxide (1.1 equiv). The mixture was stirred until total solubilization. The ethanol was completely removed in vacuum and the residual was dissolved in acetone (250 mL) followed by adding benzenesulfonyl chloride (1.1 equiv, 110 mmol). The reaction mixture was stirred for half hour. The precipitate was filtered off and the filtrate was concentrated and recrystallized from methanol to give a white solid. Yield: 33percent. To a solution of indole 3-carboxaldehyde (8y) (100 mmol) in ethanol (500 mL) at RT was added potassium hydroxide (1.1 equiv). The mixture was stuffed until total solubilization. The ethanol was completely removed in vacuum and the residual was dissolved in acetone (250 mL) followed by adding benzenesulfonyl chloride (1.1 equiv, 110 mmol). The reaction mixture was stuffed forhalf hour. The precipitate was filtered off and the filtrate was concentrated and recrystallized from methanol to give a white solid. Yield: 33percent. ‘H NMR (500 MHz, CDC13) ö 10.17 (s, 1 H), 8.25-8.39 (m, 2 H), 7.97-8.09 (m, 3 H), 7.69 (t, J= 7.33 Hz, 1 H), 7.59 (t, J= 7.5 Hz, 2 H), 7.39 -7.54 (m, 2 H). MS (ESI) calcd for C, 5H, , N035 285.1, found 286.0 [M + Hf’.

Molecular Weight:285.3
XLogP3:2.7
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:3
Exact Mass:285.04596439
Monoisotopic Mass:285.04596439
Topological Polar Surface Area:64.5
Heavy Atom Count:20
Complexity:450
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes