[3-[4-Chloro-2-(2,6-difluorobenzoyl)phenyl]prop-2-ynyl]carbamic acid tert-butyl ester

Base Information

• Chemical Name: [3-[4-Chloro-2-(2,6-difluorobenzoyl)phenyl]prop-2-ynyl]carbamic acid tert-butyl ester
• CAS No.: 869366-03-0
• Molecular Formula: C21H18 Cl F2 N O3
• Molecular Weight: 405.829
• Hs Code.: 2924299090
• Mol file: 869366-03-0.mol

Synonyms:[3-[4-Chloro-2-(2,6-difluorobenzoyl)phenyl]prop-2-ynyl]carbamicacid tert-butyl ester

Chemical Property of [3-[4-Chloro-2-(2,6-difluorobenzoyl)phenyl]prop-2-ynyl]carbamic acid tert-butyl ester

Chemical Property:

• PSA: 55.40000
• LogP: 5.11630

Purity/Quality:

98%min ^*data from raw suppliers

tert-Butyl (3-(4-chloro-2-(2,6-difluorobenzoyl)-phenyl)prop-2-yn-1-yl)carbamate 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of [3-[4-Chloro-2-(2,6-difluorobenzoyl)phenyl]prop-2-ynyl]carbamic acid tert-butyl ester

There total 4 articles about [3-[4-Chloro-2-(2,6-difluorobenzoyl)phenyl]prop-2-ynyl]carbamic acid tert-butyl 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: 61.0%

(5-chloro-2-iodophenyl)(2,6-difluorophenyl)methanone (869365-97-9) + N-tert-Butoxycarbonyl-1-amino-3-propyne (92136-39-5) → tert-butyl (3-(4-chloro-2-(2,6-difluorobenzoyl)phenyl)prop-2-yn-1-yl)carbamate (869366-03-0)

Guidance literature:

(5-chloro-2-iodophenyl)(2,6-difluorophenyl)methanone; N-tert-Butoxycarbonyl-1-amino-3-propyne; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; In dichloromethane; for 0.5h;

With diethylamine; In dichloromethane; at 20 ℃; for 16h;

Reference yield:

(2-amino-5-chlorophenyl)-(2,6-difluorophenyl)methanone (28910-83-0) → tert-butyl (3-(4-chloro-2-(2,6-difluorobenzoyl)phenyl)prop-2-yn-1-yl)carbamate (869366-03-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: acetic acid; hydrogenchloride; sodium nitrite / water / 1.5 h / 9 °C / Inert atmosphere

1.2: 1.5 h / 9 - 20 °C / Inert atmosphere

2.1: copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride; triethylamine / dichloromethane / 8 h / 0 - 20 °C / Inert atmosphere

With hydrogenchloride; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; acetic acid; triethylamine; sodium nitrite; In dichloromethane; water; 2.1: |Sonogashira Cross-Coupling;

DOI:10.1021/ml500409n

Reference yield:

tert-butyl (4-chloro-2-(2,6-difluorobenzoyl)phenyl)carbamate (869365-92-4) → tert-butyl (3-(4-chloro-2-(2,6-difluorobenzoyl)phenyl)prop-2-yn-1-yl)carbamate (869366-03-0)

Guidance literature:

Multi-step reaction with 3 steps

1.1: trifluoroacetic acid / dichloromethane / 0 - 20 °C / Inert atmosphere

2.1: hydrogenchloride; acetic acid; sodium nitrite / water / 0 - 5 °C / Inert atmosphere

2.2: 0 - 20 °C / Inert atmosphere

3.1: copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride / dichloromethane / 0.5 h / Inert atmosphere

3.2: 16 h / 20 °C / Inert atmosphere

With hydrogenchloride; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; acetic acid; trifluoroacetic acid; sodium nitrite; In dichloromethane; water; 3.1: Sonogashira coupling / 3.2: Sonogashira coupling;

DOI:10.1002/anie.201200994

upstream raw materials:

(5-chloro-2-iodophenyl)(2,6-difluorophenyl)methanone

N-tert-Butoxycarbonyl-1-amino-3-propyne

tert-butyl (4-chloro-2-(2,6-difluorobenzoyl)phenyl)carbamate

N-(t-butoxycarbonyl)-4-chloroaniline

Downstream raw materials:

4-{[9-chloro-7-(2,6-difluorophenyl)-5H-pyrimido[5,4-d][2]benzazepin-2-yl]amino}benzoic acid

tert-butyl (1-(2-(4-((9-chloro-7-(2,6-difluorophenyl)-5H-benzo[c]pyrimido[4,5-e]azepin-2-yl)amino)benzamido)ethyl)piperidin-4-yl)carbamate

N-(2-(4-aminopiperidin-1-yl)ethyl)-4-((9-chloro-7-(2,6-difluorophenyl)-5H-benzo[c]pyrimido[4,5-e]azepin-2-yl)amino)benzamide

8-chloro-4-[(dimethylamino)methylene]-1-(2,6-difluorophenyl)-3,4-dihydro-5H-2-benzazepin-5-one

Refernces

• 1、 Yang, Katherine S.,Budin, Ghyslain,Reiner, Thomas,Vinegoni, Claudio,Weissleder, Ralph. "Bioorthogonal imaging of Aurora Kinase A in live cells". supporting information; experimental part. p. 6598 - 6603. Retrieved 2012/09/22.