Binap, (A+-)- → HCID 90041121, 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 (0.221 g, 0.5 mmol), 3-methyl-isothiazol-5-ylamine hydrochloride (0.151 g, 1 mmol), tris(dibenzylideneacetone)dipalladium (0.023 g, 0.025 mmol), racemic BINAP [rac-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl](0.047 g, 0.075 mmol) and sodium tert-butoxide (0.144 g, 1.5 mmol) in toluene (3.5 mL), under an argon atmosphere, was heated and stirred in a sealed vessel at 110° C. for 19 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, then repeated with 50% ethyl acetate in hexanes, and again with 40% ethyl acetate I hexanes) gave 3-methyl-2-(3-methyl-isothiazol-5-ylamino)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid tert-butylamide (0.101 g, 43%) as a yellow solid. 1H NMR (400 MHz, DMSO-d6) δ ppm −0.08 (s, 9H), 0.84 (t, J=8.0 Hz, 2H), 1.55 (s, 9H), 2.35 (s, 3H), 2.67 (s, 3H), 3.53 (t, J=8.0 Hz, 2H), 5.61 (s, 2H), 6.94 (s, 1H), 7.34 (s, 1H), 8.25 (s, 1H), 10.49 (s, 1H). MS (EI/CI) m/z: 475 [M+H].

Provenance & Evidence