tert-Butyl 5-formyl-1H-indole-1-carboxylate

Base Information

• Chemical Name: tert-Butyl 5-formyl-1H-indole-1-carboxylate
• CAS No.: 279256-09-6
• Molecular Formula: C14H15 N O3
• Molecular Weight: 245.278
• Hs Code.: 2933990090
• European Community (EC) Number: 806-916-4
• DSSTox Substance ID: DTXSID70457663
• Wikidata: Q82280599
• Mol file: 279256-09-6.mol

Synonyms:tert-Butyl 5-formyl-1H-indole-1-carboxylate;279256-09-6;N-boc-1H-Indole-5-carbaldehyde;Tert-butyl 5-formylindole-1-carboxylate;SCHEMBL1056190;DTXSID70457663;KDMYWOVAHWERQN-UHFFFAOYSA-N;1-Boc-1H-Indole-5-carboxaldehyde;N-tert-butoxycarbonyl-5-formylindole;AR3440;MFCD09029796;AKOS015957397;1-(t-Butyloxycarbonyl)-5-formylindole;AM86074;MB06800;SS-6028;1-BOC-1H-INDOLE-5-CARBALDEHYDE;Tert-butyl 5-formyl-1H-indol-1-carboxyate;BB 0256632;CS-0003916;EN300-235029;A853159;F2184-0215;5-FORMYL-INDOLE-1-CARBOXYLIC ACID TERT-BUTYL ESTER

Chemical Property of tert-Butyl 5-formyl-1H-indole-1-carboxylate

Chemical Property:

• Melting Point: 58-60 °C
• Boiling Point: 380.0±34.0 °C(Predicted)
• PSA: 48.30000
• Density: 1.13±0.1 g/cm3(Predicted)
• LogP: 3.23700
• Storage Temp.: 2-8°C
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 245.10519334
• Heavy Atom Count: 18
• Complexity: 334

Purity/Quality:

99.3% ^*data from raw suppliers

TERT-BUTYL 5-FORMYL-1H-INDOLE-1-CARBOXYLATE 95% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)N1C=CC2=C1C=CC(=C2)C=O

Technology Process of tert-Butyl 5-formyl-1H-indole-1-carboxylate

There total 9 articles about tert-Butyl 5-formyl-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: 100.0%

1H-indole-5-carboxaldehyde (1196-69-6) + di-tert-butyl dicarbonate (24424-99-5) → 1-(tert-butyloxycarbonyl)indole-5-carboxaldehyde (279256-09-6)

Guidance literature:

With potassium tert-butylate; at 0 - 20 ℃; for 72h;

DOI:10.1021/jo025964i

Reference yield: 63.0%

Glyoxilic acid (298-12-4) + (1-(tert-butoxycarbonyl)-1H-indol-5-yl)boronic acid (317830-84-5) → 1-(tert-butyloxycarbonyl)indole-5-carboxaldehyde (279256-09-6)

Guidance literature:

With 1,2,3,4-tetrahydroisoquinoline; In acetonitrile; at 20 ℃; Green chemistry;

DOI:10.1002/anie.201703127

Reference yield: 55.0%

2,2-diethoxy acetic acid (20461-86-3) + 5-bromo-indole-1-carboxylic acid tert-butyl ester (182344-70-3) → 1-(tert-butyloxycarbonyl)indole-5-carboxaldehyde (279256-09-6)

Guidance literature:

With nickel(II) chloride hexahydrate; (4s,6s)-2,4,5,6-tetra(9H-carbazol-9-yl)isophthalonitrile; caesium carbonate; 4,4'-di-tert-butyl-2,2'-bipyridine; In N,N-dimethyl-formamide; at 20 ℃; for 24h; Schlenk technique; Inert atmosphere; Irradiation;

DOI:10.1002/anie.201610108

upstream raw materials:

1H-indole-5-carboxaldehyde

di-tert-butyl dicarbonate

1-(tert-butoxycarbonyl)-1H-indole-5-carbonitrile

1H-indole-5-carbonitrile

Downstream raw materials:

(E)-2-methyl-3-(1-tert-butyloxycarbonyl-1H-indol-5-yl)-1-(3,4,5-trimethoxyphenyl)prop-2-en-1-one

(E)-2-methyl-3-(1-tert-butyloxycarbonyl-1H-indol-5-yl)-1-(2,5-dimethoxyphenyl)prop-2-en-1-one

Refernces

• 1、 Kock, Mario,Fresia, Marvin,Jones, Peter G.,Lindel, Thomas. "Synthesis of Raputimonoindoles A–C and Congeners". supporting information. p. 4061 - 4065. Retrieved 2019/06/27.
• 2、 Wang, Qinghui,Arnst, Kinsie E.,Wang, Yuxi,Kumar, Gyanendra,Ma, Dejian,White, Stephen W.,Miller, Duane D.,Li, Wei,Li, Weimin. "Structure-guided design, synthesis, and biological evaluation of (2-(1 H-Indol-3-yl)-1 H-imidazol-4-yl)(3,4,5-trimethoxyphenyl) methanone (ABI-231) analogues targeting the colchicine binding site in Tubulin". . p. 6734 - 6750. Retrieved 2019/08/20.