(1-(Tert-butoxycarbonyl)-5-methoxy-1H-indol-2-YL)boronic acid

Base Information

• Chemical Name: (1-(Tert-butoxycarbonyl)-5-methoxy-1H-indol-2-YL)boronic acid
• CAS No.: 290331-71-4
• Molecular Formula: C14H18BNO5
• Molecular Weight: 291.112
• Hs Code.: 2933990090
• European Community (EC) Number: 691-691-3
• DSSTox Substance ID: DTXSID60383346
• Nikkaji Number: J1.365.110H
• Wikidata: Q72449873
• Mol file: 290331-71-4.mol

Synonyms:290331-71-4;1-(tert-butoxycarbonyl)-5-methoxy-1H-indol-2-ylboronic acid;(1-(TERT-BUTOXYCARBONYL)-5-METHOXY-1H-INDOL-2-YL)BORONIC ACID;1-BOC-5-METHOXYINDOLE-2-BORONIC ACID;N-Boc-5-methoxy-2-indolylboronic acid;1-BOC-5-METHOXY-1H-INDOLE-2-BORONIC ACID;N-Boc-5-methoxyindole-2-boronic acid;[5-methoxy-1-[(2-methylpropan-2-yl)oxycarbonyl]indol-2-yl]boronic Acid;1H-INDOLE-1-CARBOXYLIC ACID, 2-BORONO-5-METHOXY-, 1-(1,1-DIMETHYLETHYL) ESTER;[1-(tert-butoxycarbonyl)-5-methoxy-1h-indol-2-yl]boronic acid;SCHEMBL1497620;DTXSID60383346;PZLVPMBCKHDVKT-UHFFFAOYSA-N;MFCD04039006;AKOS004116258;AB17239;AM86838;N-Boc-5-methoxy-indole-2-boronic acid;AS-38803;CS-0002271;FT-0644355;(2,5,7-trimethyl-1H-indol-3-yl)aceticacid;A22960;N-Boc-5-methoxy-2-indolylboronic acid, >=95%;J-017365;5-Methoxy-1H-indole-2-boronic acid, N-BOC protected;1-(tert-butoxycarbonyl)-5-methoxy-indole-2-boronic acid;1-(tert-butoxycarbonyl)-5-methoxyindole-2-boronic acid;1-(tert butoxy carbonyl) 5-methoxy-1H-indol-2-yl-boronic acid;1-(tert butoxy carbonyl) 5-methoxy-1H-indol-2yl-boronic acid;[5-Methoxy-1-(tert-butoxycarbonyl)-1H-indole-2-yl]boronic acid;(1-(TERT-BUTOXYCARBONYL)-5-METHOXY-1H-INDOL-2-YL)BORONICACID

Chemical Property of (1-(Tert-butoxycarbonyl)-5-methoxy-1H-indol-2-YL)boronic acid

Chemical Property:

• Vapor Pressure: 7.3E-10mmHg at 25°C
• Melting Point: 102-107 °C
• Refractive Index: 1.535
• Boiling Point: 475.9 °C at 760 mmHg
• PKA: 8.00±0.30(Predicted)
• Flash Point: 241.6 °C
• PSA: 80.92000
• Density: 1.19 g/cm³
• LogP: 1.11290
• Storage Temp.: 2-8°C
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 291.1278028
• Heavy Atom Count: 21
• Complexity: 384

Purity/Quality:

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

1-BOC-5-methoxyindole-2-boronicacid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B(C1=CC2=C(N1C(=O)OC(C)(C)C)C=CC(=C2)OC)(O)O
• Uses: Reactant for:Preparation of dihalogenated pyrazoles via dipolar cycloaddition by palladium-catalyzed cross-coupling processesSuzuki-Miyaura cross-couplingSynthesis of the isocryptolepine alkaloid and its related skeletons using a modified Pictet-Spengler reaction

Technology Process of (1-(Tert-butoxycarbonyl)-5-methoxy-1H-indol-2-YL)boronic acid

There total 5 articles about (1-(Tert-butoxycarbonyl)-5-methoxy-1H-indol-2-YL)boronic 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: 96.0%

1-(tert-butyloxycarbonyl)-5-methoxyindole (99275-47-5) → 1-(tert-butoxycarbonyl)-5-methoxy-1H-indol-2-ylboronic acid (290331-71-4)

Guidance literature:

1-(tert-butyloxycarbonyl)-5-methoxyindole; With Triisopropyl borate; lithium diisopropyl amide; In tetrahydrofuran; at 0 ℃; for 2h;

With phosphate buffer; In tetrahydrofuran; pH=6.0; Further stages.;

DOI:10.1021/jo070206j

Reference yield:

Triisopropyl borate (5419-55-6) + 1-(tert-butyloxycarbonyl)-5-methoxyindole (99275-47-5) → 1-(tert-butoxycarbonyl)-5-methoxy-1H-indol-2-ylboronic acid (290331-71-4)

Guidance literature:

Triisopropyl borate; 1-(tert-butyloxycarbonyl)-5-methoxyindole; With lithium diisopropyl amide; In tetrahydrofuran; at 0 ℃; for 1.16667h;

With hydrogenchloride; water; In tetrahydrofuran; hexanes;

Reference yield:

5-methoxylindole (1006-94-6) → 1-(tert-butoxycarbonyl)-5-methoxy-1H-indol-2-ylboronic acid (290331-71-4)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 4-(N,N-dimethylamino)pyridine / CH₂Cl₂ / 1 h / 20 °C

2.1: triisopropyl borate; LDA / tetrahydrofuran / 2 h / 0 °C

2.2: 96 percent / aq. phosphate buffer / tetrahydrofuran / pH 6.0

With dmap; Triisopropyl borate; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jo070206j

upstream raw materials:

1-(tert-butyloxycarbonyl)-5-methoxyindole

5-methoxylindole

di-tert-butyl dicarbonate

Triisopropyl borate

Downstream raw materials:

C₂₉H₃₀N₂O₅S

3-bromo-5-[N-Boc-5-methoxyindol]-2-yl-1-(4-methoxyphenyl)-1H-pyrazole

5-methoxyindolin-2-one

Refernces

• 1、 -. "CYCLOHEXYL AMIDE DERIVATIVES AS CRF RECEPTOR ANTAGONISTS". . . Retrieved 2016/02/02.
• 2、 Mizuta, Masahiro,Seio, Kohji,Miyata, Kenichi,Sekine, Mitsuo. "Fluorescent pyrimidopyrimidoindole nucleosides: Control of photophysical characterizations by substituent effects". . p. 5046 - 5055. Retrieved 2008/02/08.