Category: 20289-27-4

20289-27-4, 7-(Benzyloxy)-1H-indole is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

a) 1-Methyl-indol-7-ol A mixture of 7-benzyloxyindole (300 mg, 1.34 mmol), dimethyl oxalate (317 mg, 2.68 mmol) and potassium tert-butoxide (302 mg, 2.68 mmol) in 5 mL DMF was stirred at 110 C. overnight. The solution was poured into NaHCO3 saturated solution (20 mL) and extracted with EtOAc. The organic layer was separated, washed with brine and dried over Na2SO4. The solvent was removed in vacuo to yield 200 mg of 7-benzyloxy-1-methylindole, which was hydrogenated by 5% Pd/C in 20 mL methanol under H2 (50 psi) to yield 90 mg (45.5%) of the title compound. 1H NMR (CDCl3): 7.19-7.16 (m, 1H), 6.94 (d, J=3 Hz, 1H), 6.86 (t, J=7.5 Hz, 1H), 6.48-6.46 (m, 1H), 6.40 (d, J=3 Hz, 1H), 5.05 (s, 1H), 4.07 (s, 3H).

20289-27-4, As the paragraph descriping shows that 20289-27-4 is playing an increasingly important role.

Reference：
Patent; Cytovia, Inc.; US2003/65018; (2003); A1;,
Indole alkaloid derivatives as building blocks of natural products from?Bacillus thuringiensis?and?Bacillus velezensis?and their antibacterial and antifungal activity study
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

20289-27-4, 7-(Benzyloxy)-1H-indole is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

EXAMPLE 93 Preparation of 7-Benzyloxy-3-{4-[(1H-2-methylimidazo[4,5-c]pyrid-1-yl)methyl]benzoyl}indole The desired compound was prepared according to the method of Example 90, except substituting 7-benzyloxyindole for 4,7-dimethoxycarbonylindole. 1 H NMR (DMSO-d6, 300 MHz) delta2.59 (s, 3H), 5.30 (s, 2H), 5.63 (s, 2H), 6.93 (d, 1H, J=7.7 Hz), 7.13 (t, 1H, J=7.9 Hz), 7.28 (d, 2H, J=8.1 Hz), 7.32-7.46 (c, 3H), 7.54-7.60 (c, 2H), 7.62 (d, 1H, J=5.1 Hz), 7.71 (d, 1H, J=2.2 Hz), 7.76 (d, 2H), J=8.5 Hz), 7.80 (d, 1H, J=8.1 Hz), 8.30 (d, 1H, J=5.2 Hz), 8.87 (s, 1H), 12.24 (d, 1H, J=2.6 Hz). MS (DCI/NH3) m/e 473 (M+H)+. IR, cm-1 (microscope) 738 (m), 1219 (m), 1248 (m), 1278 (m), 1436 (s). Anal calcd for C30 H24 N4 O2.1.2 H2 O: C, 72.92; H, 5.38; N, 11.34. Found: C, 72.97; H, 5.30; N, 11.05., 20289-27-4

20289-27-4 7-(Benzyloxy)-1H-indole 260798, aindole-building-block compound, is more and more widely used in various fields.

Reference：
Patent; Abbott Laboratories; US5486525; (1996); A;,
Indole alkaloid derivatives as building blocks of natural products from?Bacillus thuringiensis?and?Bacillus velezensis?and their antibacterial and antifungal activity study
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.20289-27-4,7-(Benzyloxy)-1H-indole,as a common compound, the synthetic route is as follows.

Intermediate 32 Preparation of N-acetyltryotophan acetic anhydride (0.5 ML, 5.2 mmol) was added to a slurry of Intermediate 31 (0.575 g, 2.6 mmol) and DL-serine (0.270 g, 2.6 mmol) in anhydrous acetic acid (5 ML) at room temperature under a nitrogen blanket.The resulting orange solution was heated to reflux and stirred for 24 hours.The cooled mixture then was concentrated under reduced pressure to provide the intermediate N-acetyltryptophan as dark red oil, which was used immediately without purification

20289-27-4, 20289-27-4 7-(Benzyloxy)-1H-indole 260798, aindole-building-block compound, is more and more widely used in various fields.

Reference：
Patent; Orme, Mark W.; Sawyer, Jason Scott; Daugan, Alain Claude-Marie; US2003/225092; (2003); A1;,
Indole alkaloid derivatives as building blocks of natural products from?Bacillus thuringiensis?and?Bacillus velezensis?and their antibacterial and antifungal activity study
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

20289-27-4, 7-(Benzyloxy)-1H-indole is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

A solution of 7-benzyloxy-1H-indole (1.0 g, 4.5 mmol) in DMF (30 mL) stirred at 0 C. under N2 was treated with NaH (215 mg, 5.4 mmol). After 30 min, CH3I (1.3 g, 9.0 mmol) was added. The reaction was warmed up to RT and stirred for 1 hour. The reaction mixture was quenched with water and extracted with DCM (25 mL*2). The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluting with PE) to give the title compound as a colorless oil in 94% yield. 1H NMR (300 MHz, CDCl3): delta 7.42-7.40 (m, 2H), 7.36-7.29 (m, 3H), 7.09 (d, J=8.1 Hz, 1H), 6.90 (d, J=2.7 Hz, 1H), 6.86 (t, J=7.8 Hz, 1H), 6.62 (d, J=7.5 Hz, 1H), 6.32 (d, J=3.0 Hz, 1H), 5.06 (s, 2H), 3.92 (s, 3H). LCMS (M+H)+238.

20289-27-4, The synthetic route of 20289-27-4 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; CELGENE QUANTICEL RESEARCH, INC.; Bennett, Michael John; Betancort, Juan Manuel; Boloor, Amogh; Kanouni, Toufike; Stafford, Jeffrey Alan; Veal, James Marvin; Wallace, Michael Brennan; (250 pag.)US2017/298040; (2017); A1;,
Indole alkaloid derivatives as building blocks of natural products from?Bacillus thuringiensis?and?Bacillus velezensis?and their antibacterial and antifungal activity study
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.20289-27-4,7-(Benzyloxy)-1H-indole,as a common compound, the synthetic route is as follows.

EXAMPLE 5 Preparation of 3(Pyridin-3-yl)-7-(7-phenylmethoxyindol-3-yl)carbonyl-1H,3H-pyrrolo[1,2-c]thiazole The title compound was prepared by the procedure described in Example 1 using 7-phenylmethoxyindole instead of indole. The crude product was purified by flash chromatography (15 p.s.i.) on 250 g silica gel eluding with 1:1 THF/hexane and then recrystallized from ethyl acetate/ether to afford the title compound. m.p. 184-188 C. 1 H NMR (DMSO-d6, 300 MHz) delta4.45 (d, J=15 Hz, 1H), 4.62 (dd, J=15, 2 Hz, 1H), 6.68 (d, J=3 Hz, 1H), 6.76 (d, J=1 Hz, 1H), 6.85 (d, J=3 Hz, 1H), 6.89 (d, J=8 Hz, 1H), 7.08 (t, J=8 Hz, 1H), 7.31-7.46 (m, 4H), 7.56-7.67 (m, 3H), 7.83 (d, J=8 Hz, 1H), 8.03 (d, J=3 Hz, 1H), 8.53-8.58 (m, 2H), 12.06 (d, J=3 Hz). Anal calcd for C27 H21 N3 O2 S: C, 71.82; H, 4.69; N, 9.31. Found: C, 71.33; H, 4.70; N, 9.16. MS (DCI/NH3) m/e 452 (M+H)+.

20289-27-4, The synthetic route of 20289-27-4 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; Abbott Laboratories; US5459152; (1995); A;,
Indole alkaloid derivatives as building blocks of natural products from?Bacillus thuringiensis?and?Bacillus velezensis?and their antibacterial and antifungal activity study
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

20289-27-4, 7-(Benzyloxy)-1H-indole is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Furthermore, 7-benzyloxyindole (404 mg, 1.81 mmol) was hydrogenated over 10% palladium on carbon (40 mg) in EtOH (4.2 mL) at ambient temperature under atmosphere pressure for 6 h. The catalyst was filtered off and washed with EtOH. The filtrate was concentrated to give 7-hydroxyindole as pale purple crystals, which was rapidly and directly used for the next reaction., 20289-27-4

The synthetic route of 20289-27-4 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; Brigham and Women’s Hospital, Inc.; President and Fellows of Harvard College; US2005/119260; (2005); A1;,
Indole alkaloid derivatives as building blocks of natural products from?Bacillus thuringiensis?and?Bacillus velezensis?and their antibacterial and antifungal activity study
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles