Tert-butyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-YL)-1H-indazole-1-carboxylate

Base Information

• Chemical Name: Tert-butyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-YL)-1H-indazole-1-carboxylate
• CAS No.: 864771-44-8
• Molecular Formula: C18H25 B N2 O4
• Molecular Weight: 344.218
• Hs Code.: 2934999090
• ChEMBL ID: CHEMBL3236908
• DSSTox Substance ID: DTXSID40594615
• Wikidata: Q72449663
• Mol file: 864771-44-8.mol

Synonyms:864771-44-8;TERT-BUTYL 5-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-1H-INDAZOLE-1-CARBOXYLATE;1-BOC-1H-INDALZOLE-5-BORONIC ACID PINACOL ESTER;tert-butyl 5-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole-1-carboxylate;tert-butyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)indazole-1-carboxylate;MFCD08437629;1-BOC-INDAZOLE-5-BORONIC ACID PINACOL ESTER;1-BOC-INDAZOLE-5-BORONIC ACID, PINACOL ESTER;1-Boc-5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole;1H-INDAZOLE-1-CARBOXYLIC ACID, 5-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-, 1,1-DIMETHYLETHYL ESTER;5-(4,4,5,5-TETRAMETHYL-[1,3,2]DIOXABOROLAN-2-YL)-INDAZOLE-1-CARBOXYLIC ACID TERT-BUTYL ESTER;SCHEMBL760664;CHEMBL3236908;DTXSID40594615;MMXDKXUKSKMROG-UHFFFAOYSA-N;(1-(TERT-BUTOXYCARBONYL)-1H-INDAZOL-5-YL)BORONIC ACID PINACOL ESTER;AKOS005259549;AM85286;MB06151;DS-13232;SY106734;B5992;CS-0030604;N-Boc-indazole-5-boronic acid pinacol ester;A22788;P10588;EN300-7357305;1-N-BOC-INDAZOLE-5-BORONIC ACID PINACOL ESTER;1-BOC-1H-INDAZOLE-5-BORONIC ACID PINACOL ESTER;1-(tert-Butoxycarbonyl)-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)indazole;1-Boc-5-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)indazole, contains isomer;t-butyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1h-indazole-1-carboxylate;tert-Butyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxa-borolan-2-yl)-1H-indazole-1-carboxylate;tert-butyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole-1-carboxylate;tert.-butyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole-1 carboxylate;1,1-dimethylethyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole-1-carboxylate;5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)indazole-1-carboxylic acid tert-butyl ester;TERT-BUTYL5-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-1H-INDAZOLE-1-CARBOXYLATE

Chemical Property of Tert-butyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-YL)-1H-indazole-1-carboxylate

Chemical Property:

• Vapor Pressure: 1.08E-08mmHg at 25°C
• Melting Point: 110 °C
• Refractive Index: 1.537
• Boiling Point: 461.4°C at 760 mmHg
• Flash Point: 232.8°C
• PSA: 62.58000
• Density: 1.13g/cm³
• LogP: 3.11870
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 3
• Exact Mass: 344.1907374
• Heavy Atom Count: 25
• Complexity: 516

Purity/Quality:

99%, ^*data from raw suppliers

1-Boc-indazole-5-boronic acid, pinacol ester ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22-36/37/38
• Safety Statements: 22-26-36/37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B1(OC(C(O1)(C)C)(C)C)C2=CC3=C(C=C2)N(N=C3)C(=O)OC(C)(C)C

Technology Process of Tert-butyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-YL)-1H-indazole-1-carboxylate

There total 4 articles about Tert-butyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-YL)-1H-indazole-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: 87.3%

tert-butyl 5-bromo-1H-indazole-1-carboxylate (651780-02-8) + bis(pinacol)diborane (73183-34-3) → 1,1-dimethylethyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole-1-carboxylate (864771-44-8)

Guidance literature:

tert-butyl 5-bromo-1H-indazole-1-carboxylate; With palladium (II) [1,1'-bis(diphenylphosphanyl)ferrocene] dichloride; anhydrous potassium acetate; In acetonitrile; at 20 ℃; for 0.25h;

4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl-4',4',5',5'-tetramethyl-1,3,2-dioxaborolane; In acetonitrile; at 78 ℃; for 0.666667h;

DOI:10.1134/S0022476621090043

Reference yield: 74.0%

→ 1,1-dimethylethyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole-1-carboxylate (864771-44-8)

Guidance literature:

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → 1,1-dimethylethyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole-1-carboxylate (864771-44-8)

Guidance literature:

Multi-step reaction with 2 steps

1.1: dmap; triethylamine / acetonitrile / 20 °C

2.1: anhydrous potassium acetate / palladium (II) [1,1'-bis(diphenylphosphanyl)ferrocene] dichloride / dimethyl sulfoxide / 0.25 h / 20 °C

2.2: 2.5 h / 85 °C

With dmap; anhydrous potassium acetate; triethylamine; palladium (II) [1,1'-bis(diphenylphosphanyl)ferrocene] dichloride; In dimethyl sulfoxide; acetonitrile;

upstream raw materials:

tert-butyl 5-bromo-1H-indazole-1-carboxylate

bis(pinacol)diborane

di-tert-butyl dicarbonate

5-bromo-1H-indazole

Downstream raw materials:

C₃₃H₃₄F₂N₄O₃

5-{5-[4-tert-butoxycarbonyl-2S-(4-fluoro-phenyl)-piperazin-1-ylmethyl]-pyridin-3-yl}-indazole-1-carboxylic acid tert-butyl ester

1-(tert-butoxycarbonyl)-1H-indazol-5-ylboronic acid

methyl 2-((4-(1H-indazol-5-yl)-3-methyl-1-(2-methylphenyl)-1H-pyrazol-5-yl)amino)-5-methoxybenzoate

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