N,N-Dimethylglycine → HCID 44199957, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 1-[2-Bromo-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-2,2-dimethyl-propan-1-one (0.25 g, 0.61 mmol), benzenesulfonamide (0.143 g, 0.91 mmol, 1.5 equiv.), CuI (0.023 g, 0.12 mmol, 20 mol %), N,N-dimethylglycine (0.013 g, 0.12 mmol, 20 mol %) and K3PO4 (0.323 g, 1.53 mmol, 2.5 equiv.) in DMF (2 mL) was heated under an argon atmosphere in a microwave oven at 153° C. overnight. After cooling to room temperature, the reaction mixture was diluted with H2O and extracted with DCM. The combined organic extracts was washed with H2O and concentrated. The residue was purified by flash column chromatography on silica gel with EtOAc in hexane (15% to 50% gradient over 20 min) to give 0.215 g of product as a pale yellow foam. 1H NMR (CDCl3): δ 8.50 (s, 1H), 8.29 (s, 1H), 7.99-7.96 (m, 2H), 7.61-7.47 (m, 3H), 5.67 (s, 2H), 2.64-3.58 (m, 2H), 1.38 (s, 9H), 1.00-0.94 (m, 2H), 0 (s, 9H); MS [M+H]+: 489.

Provenance & Evidence