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[ CAS No. 155302-27-5 ] {[proInfo.proName]}

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Chemical Structure| 155302-27-5
Chemical Structure| 155302-27-5
Structure of 155302-27-5 * Storage: {[proInfo.prStorage]}
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Product Details of [ 155302-27-5 ]

CAS No. :155302-27-5 MDL No. :MFCD08234472
Formula : C18H22N2O2 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 298.38 Pubchem ID :-
Synonyms :

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Application In Synthesis of [ 155302-27-5 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 155302-27-5 ]

[ 155302-27-5 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 155302-27-5 ]
  • [ 155302-28-6 ]
YieldReaction ConditionsOperation in experiment
95% Step 2. Tert-butyl 4-(1H-indol-3-yl)piperidin-1-carboxylate (GEN1-139-2) Tert-butyl 4-(1H-indol-3-yl)-5,6-dihydropyridine-1(2H)-carboxylate (950 mg, 3.18 mmol) was added to a solution of Pd/C (10%, 200 mg) in tetrahydrofuran (5 mL) and MeOH (5 mL) and the mixture was hydrogenated under H2 atmosphere at 50C for 2 hours. The mixture was cooled to room temperature and filtered through kieselguhr. The filtrate was concentrated to obtain the desired compound (1.0 g, yield 95%) as a white solid. 1HNMR (400 MHz, CDCl3): δ 8.09 (br s, 1H), 7.63 (d, J= 7.6 Hz, 1H), 7.36 (d, J= 8.0 Hz, 1H), 7.21-7.17 (m, 1H), 7.12-7.08 (m, 1H), 6.95 (d, J = 2.0 Hz, 1H), 4.22 (br s, 2H), 3.01 -2.87 (m, 3H), 2.05-2.02 (m, 2H), 1.71-1.62 (m, 2H), 1.49 (s, 9H). MS (ESI): Rt = 1.75 min, m/z 299.4 [M-H]-; Purity: 91% 254 nm, 70% 214 nm.
91% With palladium 10% on activated carbon; hydrogen; In tetrahydrofuran; methanol; at 25℃; under 760.051 Torr; for 15h; Tert-butyl 4- (1H-indol-3-yl) -5,6-dihydropyridine-1 (2H) -carboxylate (10.0 g, 33.5 mmol) was addedto a solution of methanol (30 mL) and tetrahydrofuran (30 mL) , And then Pd / C (3.0 g, 10%) was added.Andreactedat 25 C under apressureof 1 atmH2for 15 hours.The reaction was stopped and the filtrate was dried under reduced pressure and purified by columnchromatography (petroleumether / ethyl acetate (v / v)=10/1) to give the title compound as a white solid (9.14 g, 91%).
91% With palladium 10% on activated carbon; hydrogen; In tetrahydrofuran; methanol; at 25℃; under 760.051 Torr; for 15h; A solution of tert-butyl 4- (1H-indol-3-yl) -5,6-dihydropyridine-1 (2H) -carboxylate (10.0 g, 33.5 mmol)Was added to methanol (30 mL)And tetrahydrofuran (30 mL) in a mixed solvent,Then add Pd / C (3.0 g, 10%).And reacted at 25 C under 1 atm H2 for 15 hours.Stop the reaction, filter, filtrate pressure dry spin dry,The title compound was obtained as a white solid (9.14 g, 91%) by column chromatography (petroleum ether / ethyl acetate (v / v) = 10/1).
With palladium 10% on activated carbon; hydrogen; In methanol; at 50℃; for 2h; Tert-butyl 4-(1H-indol-3-yl)-5,6-dihydropyridine-1(2H)-carboxylate (950 mg, 3.18 mmol) was added to a solution of Pd/C (10%, 200 mg) in tetrahydrofuran (5 mL) and MeOH (5 mL) and the mixture was hydrogenated under H2 atmosphere at 50C for 2 hours. The mixture was cooled to room temperature and filtered through kieselguhr. The filtrate was concentrated to obtain the desired compound (1.0 g, yield 95%) as a white solid. 1HNMR (400 MHz, CDCl3): δ 8.09 (br s, 1H), 7.63 (d, J= 7.6 Hz, 1H), 7.36 (d, J= 8.0 Hz, 1H), 7.21-7.17 (m, 1H), 7.12-7.08 (m, 1H), 6.95 (d, J = 2.0 Hz, 1H), 4.22 (br s, 2H), 3.01 -2.87 (m, 3H), 2.05-2.02 (m, 2H), 1.71-1.62 (m, 2H), 1.49 (s, 9H). MS (ESI): Rt = 1.75 min, m/z 299.4 [M-H]-; Purity: 91% 254 nm, 70% 214 nm.

  • 2
  • [ 50820-65-0 ]
  • [ 155302-27-5 ]
  • methyl 3-(1-(tert-butoxycarbonyl)-4-(1H-indol-3-yl)piperidin-4-yl)-1H-indole-5-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
71% With toluene-4-sulfonic acid; In N,N-dimethyl acetamide; at 70℃; for 16h; General procedure: To a 2.5 dr vial equipped with a stir bar was added 5.13 mg of p-TsOH (0.030 mmol, 0.100 equiv), 351.3 mg of N-H-indole (3.00 mmol, 10.0 equiv), and 42.9 mg of 1 (0.300 mmol, 1.00 equiv). To this 1.5 mL of DMA was added via syringe. The vial was capped and was stirred for given time at room temperature. The crude mixture was purified with flash silica-gel column chromatography. (Note: In case of liquid nucleophiles, p-TsOH was added last.)
  • 3
  • [ 347146-79-6 ]
  • [ 155302-27-5 ]
  • C27H27N3O4S [ No CAS ]
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