3-(Methylsulphonyl)aniline → HCID 90040870, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-bromo-3-methyl-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid tert-butylamide (0.110 g, 0.25 mmol), 3-methanesulfonyl-phenylamine (0.086 g, 0.5 mmol), tris(dibenzylideneacetone)dipalladium (0.011 g, 0.0125 mmol), racemic BINAP [rac-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl](0.023 g, 0.038 mmol) and sodium tert-butoxide (0.060 g, 0.63 mmol) in toluene (2.5 mL), under an argon atmosphere, was heated and stirred in a sealed vessel at 110° C. for 21.5 h. The cooled reaction mixture was diluted with ethyl acetate, washed once with brine, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. Purification by chromatography (silica, 75% ethyl acetate in hexanes) gave 0.107 g of slightly impure 2-(3-methanesulfonyl-phenylamino)-3-methyl-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid tert-butylamide as a yellow glass. The reaction was repeated as above, and the combined slightly impure products were purified further by chromatography (silica, 33% ethyl acetate in hexanes) to give 2-(3-methanesulfonyl-phenylamino)-3-methyl-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid tert-butylamide (0.169 g, 64%) as a light yellow solid. 1H NMR (400 MHz, DMSO-d6) δ ppm −0.07 (s, 9H), 0.85 (t, J=8.2 Hz, 2H), 1.30 (s, 9H), 2.64 (s, 3H), 3.19 (s, 3H), 3.54 (t, J=8.2 Hz, 2H), 5.59 (s, 2H), 7.49 (m, 1H), 7.56 (m, 1H), 7.62 (s, 1H), 7.96 (m, 1H), 8.05 (m, 1H), 8.16 (s, 1H), 8.74 (s, 1H). MS (EI/CI) m/z: 532 [M+H].

Provenance & Evidence