90271-86-6,90271-86-6, 5-Bromo-3-cyanoindole is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated
To a solution of ie/ -butyl 4-(4-(4,4,5,5-tetramethyl- l,3,2-dioxaborolan-2- yl)benzoyl)piperazine- l-carboxylate ( 0.2 M in 1,4-dioxane, 100 mu, 0.02 mmol), was added 5-bromo-lH-indole-3-carbonitrile(0.2 M in 1,4-dioxane, 100 mu, 0.02 mmol) and potassium phosphate solution (1 M aqueous, 100 mu, 0.1 mmol). The mixture was bubbled with nitrogen and tetrakis(triphenylphosphine)palladium (0) (0.02 M in toluene, 50 mu, 1 muiotaetaomicron) was added. The resulting mixture was put on a shaker in a glove box under nitrogen atmosphere and heated at 80 C overnight. After being cooled to rt, the mixture was diluted with 0.35 mL of brine and 0.5 mL of ethyl acetate. The organic layer was separated and the aqueous layer was extracted again with ethyl acetate (0.6 mL). The combined organic layers were concentrated and the residue was dissolved in 200 mu^ of methanol. HC1 solution (50 mu^ , 4 N in 1,4-dioxane, 0.2 mmol) was added. The mixture was put on a shaker at 50 C for 1 hour. The reaction mixture was concentrated in vacuo and the residue was dissolved in a solution of 10% N,N-diisopropylethylamine in dimethylacetamide (200 mu). 1-Hydroxycyclopropanecarboxylic acid (0.2 M in 1,4- dioxane, 120 mu, 0.024 mmol) was added, followed by BOP solution (0.5 M in 1,2- dichloroethane, 48 mu^ , 0.024 mmol). The mixture was put on a shaker at rt for 2 hour. The reaction mixture was then diluted with 0.45 mL of IN NaOH in brine and 0.5 mL of ethyl acetate. The organic layer was separated and the aqueous layer was extracted again with ethyl acetate (0.6 mL). The combined organic layers were concentrated and the residue was purified by HPLC: Water Autopurification MS -directed HPLC prep fraction collection with the following conditions Column, Waters XBridge OBD CI 8, 5muiotaeta, 19x50mm; flow rate 20ml/min; mobile phase, water with 0.1% ammonium hydroxide (A) and methanol with 0.1% ammonium hydroxide(B) running the following gradient 0 to 2mins (15%B), 2 to 6 mins (15-100%B); Detector ZQ Mass Detector in electrospray ionization mode. 5-(4-(4-(l-Hydroxycyclopropanecarbonyl)piperazine-l- carbonyl)phenyl)-lH-indole-3-carbonitrile (3.5 mg, 8.4 muiotaetaomicron, 42% yield) was obtained. MS (ESI, pos. ion) m/z: 415 (M + 1).
The synthetic route of 90271-86-6 has been constantly updated, and we look forward to future research findings.
Reference£º
Patent; FORMA THERAPEUTICS, INC.; BAIR, Kenneth, W.; LANCIA, David, R.; LI, Hongbin; LOCH, James; LU, Wei; MARTIN, Matthew, W.; MILLAN, David, S.; SCHILLER, Shawn, E.r.; TEBBE, Mark, J.; WO2014/164749; (2014); A1;,
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