1-(tert-Butoxycarbonyl)-5-methylindole

Base Information

• Chemical Name: 1-(tert-Butoxycarbonyl)-5-methylindole
• CAS No.: 129822-49-7
• Molecular Formula: C14H17NO2
• Molecular Weight: 231.294
• Hs Code.: 2933990090
• European Community (EC) Number: 624-480-1
• DSSTox Substance ID: DTXSID60462680
• Nikkaji Number: J416.469E
• Wikidata: Q82287249
• Mol file: 129822-49-7.mol

Synonyms:129822-49-7;1-(tert-Butoxycarbonyl)-5-methylindole;tert-Butyl 5-methyl-1H-indole-1-carboxylate;Tert-butyl 5-methylindole-1-carboxylate;1H-Indole-1-carboxylic acid, 5-methyl-, 1,1-dimethylethyl ester;SCHEMBL3269495;DTXSID60462680;NSPCCUXHOQOAJQ-UHFFFAOYSA-N;AMY10785;MFCD06008299;AKOS022180541;AS-71570;CS-0337979;1-(tert-Butoxycarbonyl)-5-methylindole, 97%;D84596;J-005720

Chemical Property of 1-(tert-Butoxycarbonyl)-5-methylindole

Chemical Property:

• Vapor Pressure: 0.000106mmHg at 25°C
• Refractive Index: n20/D 1.5410(lit.)
• Boiling Point: 208-209oC(lit.)
• Flash Point: >230 °F
• PSA: 31.23000
• Density: 1.056 g/mL at 25oC(lit.)
• LogP: 3.73290
• XLogP3: 3.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 231.125928785
• Heavy Atom Count: 17
• Complexity: 295

Purity/Quality:

98%min ^*data from raw suppliers

1-(tert-Butoxycarbonyl)-5-methylindole 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22-43
• Safety Statements: 36/37

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC2=C(C=C1)N(C=C2)C(=O)OC(C)(C)C
• Uses: Reactant in stereoselective preparation of substituted dihydroindole derivatives via palladium-catalyzed stereoselective carboaminoxylation reactions Reactant in conversion of 1-Boc-indoles to 1-Boc-oxindoles Reactant in preparation of indolyl aromatic chiral alpha-sulfoxides Reactant in preparation of (indolyl)borates, silanes, and silanols. Reactant in stereoselective preparation of substituted dihydroindole derivatives via palladium-catalyzed stereoselective carboaminoxylation reactionsReactant in conversion of 1-Boc-indoles to 1-Boc-oxindolesReactant in preparation of indolyl aromatic chiral alpha-sulfoxidesReactant in preparation of (indolyl)borates, silanes, and silanols

Technology Process of 1-(tert-Butoxycarbonyl)-5-methylindole

There total 5 articles about 1-(tert-Butoxycarbonyl)-5-methylindole 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%

di-tert-butyl dicarbonate (24424-99-5) + 5-methyl-1H-indole (614-96-0) → 5-methylindole-1-carboxylic acid tert-butyl ester (129822-49-7)

Guidance literature:

With dmap; In acetonitrile; at 20 ℃;

DOI:10.1039/c1ob06411h

Reference yield:

2-Hydroxy-5-methyl-2,3-dihydro-indole-1-carboxylic acid tert-butyl ester (138344-33-9) → 5-methylindole-1-carboxylic acid tert-butyl ester (129822-49-7)

Guidance literature:

With hydrogenchloride; In tetrahydrofuran; Yield given; Ambient temperature;

DOI:10.1055/s-1991-26597

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → 5-methylindole-1-carboxylic acid tert-butyl ester (129822-49-7)

Guidance literature:

Multi-step reaction with 3 steps

1: tetrahydrofuran / Heating

2: 1) s-BuLi, 2) DMF / 1) THF, cyclohexane, -40 to -20 deg C, 2) -40 deg C, 5 min

3: 12N HCl / tetrahydrofuran / Ambient temperature

With hydrogenchloride; sec.-butyllithium; N,N-dimethyl-formamide; In tetrahydrofuran;

DOI:10.1055/s-1991-26597

upstream raw materials:

2-Hydroxy-5-methyl-2,3-dihydro-indole-1-carboxylic acid tert-butyl ester

di-tert-butyl dicarbonate

5-methyl-1H-indole

(2,4-dimethylphenyl)carbamic acid tert-butyl ester

Downstream raw materials:

t-butyl 5-(bromomethyl)-1H-indole-1-carboxylate

2-(hydroxydimethylsilyl)-5-methyl-1H-indole-1-carboxylic acid 1,1-dimethylethyl ester

{1-[(tert-butoxy)carbonyl]-5-methyl-1H-indol-2-yl}boronic acid

β-D-1-(3-methyl-pyrimido[4,5-d]pyrimido[1,6-a]indol-10-yl)-5-O-(4,4'-dimethoxytrityl)-2-deoxyribose-3-(2-cyanoethyl N,N-diisopropylphosphoramidite)

Refernces

• 1、 -. "THERAPEUTIC COMPOUNDS AND METHODS TO TREAT INFECTION". Paragraph 0458-0459. . Retrieved 2019/02/13.
• 2、 Carbone, Anna,Pennati, Marzia,Parrino, Barbara,Lopergolo, Alessia,Barraja, Paola,Montalbano, Alessandra,Spanò, Virginia,Sbarra, Stefania,Doldi, Valentina,De Cesare, Michelandrea,Cirrincione, Girolamo,Diana, Patrizia,Zaffaroni, Nadia. "Novel 1H-pyrrolo[2,3-b]pyridine derivative nortopsentin analogues: Synthesis and antitumor activity in peritoneal mesothelioma experimental models". . p. 7060 - 7072. Retrieved 2013/10/01.