Lithium Hexamethyldisilazide → 8-(Benzenesulfonyl)-12-bromo-3-hydroxy-5,8,10-triazatricyclo[7.4.0.02,7]trideca-1(9),2,4,6,10,12-hexaene-4-carbonitrile

Participants

Reaction Conditions

Reaction Steps

Lithium bis(trimethylsilyl)amide (2.34 mL of a 1N solution in THF, 2.34 mmol) was added dropwise to a cooled (−78° C.) suspension of 1-benzenesulfonyl-5-bromo-2-{[cyanomethyl-(toluene-4-sulfonyl)amino]methyl}-1H-pyrrolo[2,3-b]pyridine-3-carboxylic acid methyl ester (0.48 g, 0.78 mmol) in dry THF (12 mL). The reaction mixture was allowed to slowly warm to −10° C. and then quenched with saturated aqueous ammonium chloride solution (8 mL). The reaction mixture was diluted with water and washed with DCM (2×10 mL). The combined organic phase was dried over anhydrous magnesium sulfate and concentrated in vacuo. The resultant residue was purified by flash chromatography (silica, 5 g cartridge, Si-SPE, 10-100% THF in DCM) to afford the title compound as a brown solid (0.20 g, 60%). LCMS (Method B): RT=3.83 min, M+H+=429/431.

Provenance & Evidence