Compound 26
methyl 7-(3-((4-bromo-3-formylphenoxy)methyl)-1,5-dimethyl-1H-pyrazol-4-yl)-1-methyl-3-(3-(naphthalen-1-yloxy)propyl)-1H-indole-2-carboxylate
From: Inhibition of Mcl-1 through covalent modification of a noncatalytic lysine side chain
Synthetic procedure: See article for the definitive version of this procedure and for full experimental details.
To a solution of 7-(3-((4-bromo-3-formylphenoxy)methyl)-1,5-dimethyl-1H-pyrazol-4-yl)-3-(3-(naphthalen-1-yloxy)propyl)-1H-indole-2-carboxylic acid 18 (40 mg, 0.06 mmol) in DMF (0.4 mL) was added cesium carbonate (Cs2CO3, 40 mg, 0.12 mmol) and methyl iodide (MeI, 17.4 mg, 7.64 µl, 0.12 mmol). The reaction mixture was stirred at room temperature for 2 h. Next, the reaction was diluted with ethyl acetate, washed with water, and concentrated. The crude 26 was subjected to the next reaction without purification. Crude MS-ESI (m/z): [M + H]+ calcd for C37H34BrN3O5, 680.18; found 680.3.
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316894738
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