Ethylenediaminetetraacetic Acid → HCID 22324074, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of t-BuLi (1.7 M in pentane, 25 ml, 42 mmol) in dry THF at −78° C. was added 2-bromopyridine (1.9 ml, 20 mmol) in such a rate that the temperature did not exceed −70° C. The mixture was stirred for another 30 min at −78° C. A solution of ZnCl2 (2M in THF, 30 ml, 60 mmol) was added slowly and the cooling bath was removed and warmed to 20° C. 5-Iodo-2-aminobenzenesulfonamide (see compound 37) (1.0 g, 3.2 mmol) and Pd(PPh3)4 (0.3 g, 8 mol %) was added and the mixture was refluxed for 6 h. The THF was evaporated and the residue was treated with EDTA (53 g, 0.18 mol) and made slightly basic (pH≈8–9) with 1 M NaOH followed by extraction with EtOAc (3×100 ml), drying (Na2SO4). The organic layer was concentrated to ca. 40 ml and n-hexane was added slowly. The product was filtered off, yielding 0.72 g (87%) of 2-amino-4-methyl-5-(2-pyridyl)-1-benzenesulfonamide as light-yellow crystals. The product was further transformed by Method G (using cyclohexanecarboxaldehyde). M.p. 229–231° C.

Provenance & Evidence