6-(Benzyloxy)-5-methoxy-1H-indole-2-carboxylic acid

Base Information

• Chemical Name: 6-(Benzyloxy)-5-methoxy-1H-indole-2-carboxylic acid
• CAS No.: 2495-92-3
• Molecular Formula: C17H15 N O4
• Molecular Weight: 297.31
• Hs Code.: 2933990090
• NSC Number: 92530
• DSSTox Substance ID: DTXSID80293832
• Nikkaji Number: J2.550.813K
• Wikidata: Q82032807
• Pharos Ligand ID: KJ5Z7ZF1HUFW
• ChEMBL ID: CHEMBL37880
• Mol file: 2495-92-3.mol

Synonyms:2495-92-3;6-(Benzyloxy)-5-methoxy-1H-indole-2-carboxylic acid;6-Benzyloxy-5-methoxyindole-2-carboxylic acid;6-Benzyloxy-5-methoxy-1H-indole-2-carboxylic acid;5-methoxy-6-phenylmethoxy-1H-indole-2-carboxylic acid;CHEMBL37880;NSC92530;MFCD00055977;SCHEMBL3243291;DTXSID80293832;JMOOGCFXFNKYCS-UHFFFAOYSA-N;BDBM50407310;NSC-92530;6-Benzyloxy-5-methoxy-2-carboxyindole;PD119276;Indole, 6-benzyloxy-2-carboxy-5-methoxy-;FT-0620960;6-(Benzyloxy)-5-methoxy-1H-indole-2-carboxylicacid;J-015750;6-(Benzyloxy)-5-methoxy-1H-indole-2-carboxylic acid #;6-Benzyloxy-5-methoxy-2-carboxyindole, >=99%, powder;1H-Indole-2-carboxylicacid,5-methoxy-6-(phenylmethoxy)-

Chemical Property of 6-(Benzyloxy)-5-methoxy-1H-indole-2-carboxylic acid

Chemical Property:

• Vapor Pressure: 1.3E-12mmHg at 25°C
• Melting Point: 230-232(dec.)
• Boiling Point: 542.8°Cat760mmHg
• Flash Point: 282°C
• PSA: 71.55000
• Density: 1.332g/cm³
• LogP: 3.45370
• Storage Temp.: −20°C
• Solubility.: DMSO, Methanol, Clear Yellow Solution in Pyridine @ 50mg/ml.
• XLogP3: 3.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 297.10010796
• Heavy Atom Count: 22
• Complexity: 383

Purity/Quality:

98%,99%, ^*data from raw suppliers

6-Benzyloxy-5-methoxyindole-2-carboxylic Acid ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi

MSDS Files:

Useful:

• Canonical SMILES: COC1=C(C=C2C(=C1)C=C(N2)C(=O)O)OCC3=CC=CC=C3
• Uses: Reactant for preparation of indolecarboxamides with antitumor activity in human lung cancer 1 Reactant for preparation of benzophenone- and indolecarboxylic acids as potent type-2 specific inhibitors of human steroid 5α-reductase 2 Reactant for preparation of indolecarboxamides with antitumor activity in human lung cancerReactant for preparation of benzophenone- and indolecarboxylic acids as potent type-2 specific inhibitors of human steroid 5α-reductase

Technology Process of 6-(Benzyloxy)-5-methoxy-1H-indole-2-carboxylic acid

There total 1 articles about 6-(Benzyloxy)-5-methoxy-1H-indole-2-carboxylic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

→ 5-methoxy-6-benzyloxyindole-2-carboxylic acid (2495-92-3)

Guidance literature:

4-Benzyloxy-5-methoxy-2-nitro-phenylbrenztraubensaeure, Eisen-Pulver, A., Eg. (20' Siedetemp., Ruehren);

Reference yield:

5-methoxy-6-benzyloxyindole-2-carboxylic acid (2495-92-3) → 3-[(6-hydroxy-5-methoxyindol-2-yl)carbonyl]-(1S)-(chloromethyl)-5-benzyloxy-1,2-dihydro-3H-pyrrolo[3,2-e]indole-7-carboxylic acid (736138-04-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 99 percent / H₂ / Pd/C / methanol / 2 h / 25 °C / 760 Torr

2: EDCI; NaHCO₃ / dimethylformamide / 12 h / 25 °C

3: aq. LiOH / tetrahydrofuran; methanol / 14 h / 25 °C

With lithium hydroxide; hydrogen; sodium hydrogencarbonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; palladium on activated charcoal; In tetrahydrofuran; methanol; N,N-dimethyl-formamide;

DOI:10.1021/ja0472735

Reference yield:

5-methoxy-6-benzyloxyindole-2-carboxylic acid (2495-92-3) → 3-[(6-hydroxy-5-methoxyindol-2-yl)carbonyl]-(1R)-(chloromethyl)-5-benzyloxy-1,2-dihydro-3H-pyrrolo[3,2-e]indole-7-carboxylic acid (736138-20-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 99 percent / H₂ / Pd/C / methanol / 2 h / 25 °C / 760 Torr

2: EDCI; NaHCO₃ / dimethylformamide / 12 h / 25 °C

3: aq. LiOH / tetrahydrofuran; methanol / 14 h / 25 °C

With lithium hydroxide; hydrogen; sodium hydrogencarbonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; palladium on activated charcoal; In tetrahydrofuran; methanol; N,N-dimethyl-formamide;

DOI:10.1021/ja0472735

Downstream raw materials:

5-methoxy-6-hydroxyindole-2-carboxylic acid

3-[(6-hydroxy-5-methoxyindol-2-yl)carbonyl]-(1S)-(chloromethyl)-5-benzyloxy-1,2-dihydro-3H-pyrrolo[3,2-e]indole-7-carboxylic acid

3-[(6-hydroxy-5-methoxyindol-2-yl)carbonyl]-(1R)-(chloromethyl)-5-benzyloxy-1,2-dihydro-3H-pyrrolo[3,2-e]indole-7-carboxylic acid

methyl 3-[(6-hydroxy-5-methoxyindol-2-yl)carbonyl]-(1S)-(chloromethyl)-5-benzyloxy-1,2-dihydro-3H-pyrrolo[3,2-e]indole-7-carboxylate