tert-Butyl 3-iodo-5-methoxy-1H-indole-1-carboxylate

Base Information

• Chemical Name: tert-Butyl 3-iodo-5-methoxy-1H-indole-1-carboxylate
• CAS No.: 192189-10-9
• Molecular Formula: C14H16INO3
• Molecular Weight: 373.19
• Hs Code.: 2933990090
• European Community (EC) Number: 807-737-4
• DSSTox Substance ID: DTXSID90443588
• Nikkaji Number: J2.168.696D
• Wikidata: Q82261479
• Mol file: 192189-10-9.mol

Synonyms:192189-10-9;tert-Butyl 3-iodo-5-methoxy-1H-indole-1-carboxylate;3-Iodo-5-methoxyindole-1-carboxylic acid tert-butyl ester;tert-butyl 3-iodo-5-methoxyindole-1-carboxylate;SCHEMBL14304582;DTXSID90443588;TQP1294;MFCD05864763;AKOS015911396;DS-2426;3-Iodo-5-methoxyindole, N-BOC protected;FT-0709785;A880336;tert-Butyl3-iodo-5-methoxy-1H-indole-1-carboxylate;5-Methoxy-3-iodo-1H-indole-1-carboxylic acid tert-butyl ester;1H-Indole-1-carboxylic acid, 3-iodo-5-methoxy-, 1,1-dimethylethyl ester

Chemical Property of tert-Butyl 3-iodo-5-methoxy-1H-indole-1-carboxylate

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.594
• Boiling Point: 423.312 °C at 760 mmHg
• Flash Point: 209.812 °C
• PSA: 40.46000
• Density: 1.54 g/cm³
• LogP: 4.03770
• Storage Temp.: 2-8°C(protect from light)
• XLogP3: 3.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 373.01749
• Heavy Atom Count: 19
• Complexity: 342

Purity/Quality:

97% ^*data from raw suppliers

3-Iodo-5-methoxy-1H-indole, N-Boc protected 98% ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Harmful:

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)N1C=C(C2=C1C=CC(=C2)OC)I

Technology Process of tert-Butyl 3-iodo-5-methoxy-1H-indole-1-carboxylate

There total 3 articles about tert-Butyl 3-iodo-5-methoxy-1H-indole-1-carboxylate 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: 98.0%

di-tert-butyl dicarbonate (24424-99-5) + 3-iodo-5-methoxy-1H-indole (85092-86-0) → 3-iodo-5-methoxyindole-1-carboxylic acid tert-butyl ester (192189-10-9)

Guidance literature:

With dmap; In dichloromethane; at 20 ℃; for 0.5h;

DOI:10.1016/S0040-4020(00)00773-0

Reference yield:

5-methoxylindole (1006-94-6) → 3-iodo-5-methoxyindole-1-carboxylic acid tert-butyl ester (192189-10-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 87 percent / I₂; KOH / dimethylformamide / 0.45 h / 20 °C

2: 98 percent / 4-dimethylaminopyridine / CH₂Cl₂ / 0.5 h / 20 °C

With dmap; potassium hydroxide; iodine; In dichloromethane; N,N-dimethyl-formamide; 1: Iodination / 2: Acylation;

DOI:10.1016/S0040-4020(00)00773-0

Reference yield:

5-methoxylindole (1006-94-6) + di-tert-butyl dicarbonate (24424-99-5) → 3-iodo-5-methoxyindole-1-carboxylic acid tert-butyl ester (192189-10-9)

Guidance literature:

With dmap; iodine; potassium hydroxide; In N,N-dimethyl-formamide;

DOI:10.1111/j.1747-0285.2010.00991.x

upstream raw materials:

di-tert-butyl dicarbonate

3-iodo-5-methoxy-1H-indole

5-methoxylindole

Downstream raw materials:

C₁₄H₁₈BNO₅

2-(5-methoxy-1H-indol-3-yl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine

2-(5-methoxy-1-methyl-1H-indol-3-yl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine

tert-butyl 5-methoxy-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-indole-1-carboxylate