1-(tert-Butoxycarbonyl)pyrrole-2-boronic acid MIDA ester

Base Information

• Chemical Name: 1-(tert-Butoxycarbonyl)pyrrole-2-boronic acid MIDA ester
• CAS No.: 1158984-94-1
• Molecular Formula: C14H19BN2O6
• Molecular Weight: 322.126
• Hs Code.: 2934999090
• Mol file: 1158984-94-1.mol

Synonyms:1-(tert-Butoxycarbonyl)pyrrole-2-boronic acid MIDA ester;N-Boc-pyrrole-2-boronic acid MIDA ester;tert-Butyl 2-(6-methyl-4,8-dioxo-1,3,6,2-dioxazaborocan-2-yl)-1H-pyrrole-1-carboxylate

Chemical Property of 1-(tert-Butoxycarbonyl)pyrrole-2-boronic acid MIDA ester

Chemical Property:

• Melting Point: 166-171℃
• PSA: 87.07000
• LogP: -0.06380

Purity/Quality:

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

N-Boc-pyrrole-2-boronic acid MIDA ester ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Suzuki Cross-Coupling with MIDA Boronates

Technology Process of 1-(tert-Butoxycarbonyl)pyrrole-2-boronic acid MIDA ester

There total 2 articles about 1-(tert-Butoxycarbonyl)pyrrole-2-boronic acid MIDA ester 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: 29.0%

N-tert-butyloxycarbonyl-pyrrole (5176-27-2) + N-methyliminodiacetic acid (4408-64-4) → N-Boc-pyrrole-2-boronic acid N-methyliminodiacetic acid ester (1158984-94-1)

Guidance literature:

N-tert-butyloxycarbonyl-pyrrole; With n-butyllithium; Triisopropyl borate; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; hexane; at -78 - 20 ℃;

N-methyliminodiacetic acid; In dimethyl sulfoxide; at 75 ℃; for 2h; under 1 Torr;

Reference yield:

N-methyliminodiacetic acid (4408-64-4) + N-boc-2-pyrroleboronic acid (135884-31-0) → N-Boc-pyrrole-2-boronic acid N-methyliminodiacetic acid ester (1158984-94-1)

Guidance literature:

In dimethyl sulfoxide; toluene; Dean-Stark; Reflux; Inert atmosphere; Sealed tube; Schlenk technique;

DOI:10.1002/anie.201309546

Reference yield: 90.0%

N-Boc-pyrrole-2-boronic acid N-methyliminodiacetic acid ester (1158984-94-1) + 4-tert-butoxychlorobenzene (18995-35-2) → N-(tert-butoxycarbonyl)-2-(4-tert-butoxyphenyl)pyrrole (1158985-03-5)

Guidance literature:

N-Boc-pyrrole-2-boronic acid N-methyliminodiacetic acid ester; 4-tert-butoxychlorobenzene; With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; palladium diacetate; In 1,4-dioxane; at 23 ℃; for 0.166667h; Inert atmosphere;

With potassium phosphate; water; In 1,4-dioxane; at 23 - 60 ℃; for 6.5h; Inert atmosphere;

upstream raw materials:

N-tert-butyloxycarbonyl-pyrrole

N-methyliminodiacetic acid

N-boc-2-pyrroleboronic acid

Downstream raw materials:

N-boc-2-pyrroleboronic acid

N-(tert-butoxycarbonyl)-2-(2,3-dimethoxyphenyl)pyrrole

N-(tert-butoxycarbonyl)-2-(4-tert-butoxyphenyl)pyrrole

2-(2-hydroxyphenyl)-1H-pyrrole

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