Lithium Hexamethyldisilazide → HCID 58364952, compound

Participants

Reaction Conditions

Reaction Steps

Lithium bis(trimethylsilyl)amide (220 mL of a 1N solution in THF, 220 mmol) was added dropwise to a cooled (−78° C.) suspension of 1-benzenesulfonyl-5-chloro-2-{[cyanomethyl-(toluene-4-sulfonyl)amino]methyl}-1H-pyrrolo[2,3-b]pyridine-3-carboxylic acid methyl ester (39.6 g, 69.1 mmol) in dry THF (350 mL). The reaction mixture was allowed to slowly warm to −10° C. then slowly quenched into cold 1M hydrochloric acid. The layers were separated and the aqueous layer further extracted with THF. The combined organic layer was washed with brine, dried (Na2SO4), filtered and evaporated. The resultant residue was triturated with methanol then acetone and air dried to afford the title compound as a tan solid (7.37 g, 27%). LCMS (Method B): RT=5.11 min, M+H+=385/387. 1H NMR (400 MHz, DMSO-d6): 9.23 (s, 1H), 8.76 (d, J=2.4 Hz, 1H), 8.69 (d, J=2.4 Hz, 1H), 8.19-8.19 (m, 2H), 7.75-7.75 (m, 1H), 7.62-7.61 (m, 2H).

Provenance & Evidence