Benzyl 2-methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-ylcarbamate

Base Information

• Chemical Name: Benzyl 2-methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-ylcarbamate
• CAS No.: 893440-45-4
• Molecular Formula: C20H25BN2O5
• Molecular Weight: 384.24
• Hs Code.: 2934999090
• DSSTox Substance ID: DTXSID30581630
• Nikkaji Number: J2.412.399E
• Wikidata: Q82472819
• Mol file: 893440-45-4.mol

Synonyms:893440-45-4;benzyl 2-methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-ylcarbamate;(2-METHOXY-5-(4,4,5,5-TETRAMETHYL-[1,3,2]DIOXABOROLAN-2-YL)-PYRIDIN-3-YL)CARBAMIC ACID BENZYL ESTER;benzyl N-[2-methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-yl]carbamate;benzyl (2-methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-yl)carbamate;Benzyl [2-methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-yl]carbamate;SCHEMBL397013;DTXSID30581630;LWCGCKUDTSNOON-UHFFFAOYSA-N;AM81039;benzyl 2-methoxy-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)pyridin-3-ylcarbamate;EN300-24591974;benzyl N-[2-methoxy-5-(tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-yl]carbamate;[2-Methoxy-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-pyridin-3-yl]-carbamic acid benzyl ester

Chemical Property of Benzyl 2-methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-ylcarbamate

Chemical Property:

• PSA: 82.40000
• LogP: 3.15170
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 6
• Exact Mass: 384.1856521
• Heavy Atom Count: 28
• Complexity: 523

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B1(OC(C(O1)(C)C)(C)C)C2=CC(=C(N=C2)OC)NC(=O)OCC3=CC=CC=C3

Technology Process of Benzyl 2-methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-ylcarbamate

There total 6 articles about Benzyl 2-methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-ylcarbamate 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: 92.0%

(5-iodo-2-methoxypyridin-3-yl)carbamic acid benzyl ester (893440-43-2) + bis(pinacol)diborane (73183-34-3) → [2-methoxy-5-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)pyridin-3-yl]carbamic acid benzyl ester (893440-45-4)

Guidance literature:

With bis-triphenylphosphine-palladium(II) chloride; potassium acetate; In 1,4-dioxane; Reflux; Inert atmosphere;

Reference yield:

2-hydroxy-3-aminopyridine (33630-99-8) → [2-methoxy-5-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)pyridin-3-yl]carbamic acid benzyl ester (893440-45-4)

Guidance literature:

Multi-step reaction with 4 steps

1: sodium carbonate / dichloromethane / 20 °C

2: N-iodo-succinimide / dichloromethane / Reflux

3: silver carbonate / chloroform / 20 °C / Darkness

4: bis-triphenylphosphine-palladium(II) chloride; potassium acetate / 1,4-dioxane / Reflux; Inert atmosphere

With bis-triphenylphosphine-palladium(II) chloride; N-iodo-succinimide; potassium acetate; sodium carbonate; silver carbonate; In 1,4-dioxane; dichloromethane; chloroform;

Reference yield:

(2-hydroxypyridin-3-yl)carbamic acid benzyl ester (147269-67-8) → [2-methoxy-5-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)pyridin-3-yl]carbamic acid benzyl ester (893440-45-4)

Guidance literature:

Multi-step reaction with 3 steps

1: N-iodo-succinimide / dichloromethane / Reflux

2: silver carbonate / chloroform / 20 °C / Darkness

3: bis-triphenylphosphine-palladium(II) chloride; potassium acetate / 1,4-dioxane / Reflux; Inert atmosphere

With bis-triphenylphosphine-palladium(II) chloride; N-iodo-succinimide; potassium acetate; silver carbonate; In 1,4-dioxane; dichloromethane; chloroform;

upstream raw materials:

(5-iodo-2-methoxypyridin-3-yl)carbamic acid benzyl ester

bis(pinacol)diborane

3-<<(benzyloxy)carbonyl>amino>-5-iodopyrid-2-one

2-hydroxy-3-aminopyridine

Downstream raw materials:

3-benzyloxycarbonylamino-5-[2-methylthio(4-pyrimidinyl)]-2-methoxypyridine

amrinone

2-(methyloxy)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-pyridinamine

tert-butyl 6-(5-(N-benzylcarbamate)-2-methoxypyridin-3-yl)pyrazin-2-ylmethylcarbamate