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

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

5synthesis methods

Product Name:[3-[4-Chloro-2-(2,6-difluorobenzoyl)phenyl]prop-2-ynyl]carbamic acid tert-butyl ester
CAS Number:869366-03-0
Molecular formula:C21H18ClF2NO3
Molecular Weight:405.82

869365-97-9 Synthesis

(5-CHLORO-2-IODOPHENYL) 2,6-DIFLUOROPHENYL METHANO

869365-97-9
56 suppliers
$75.00/100mg

92136-39-5 Synthesis

92136-39-5
203 suppliers
$6.00/1g

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

869366-03-0
17 suppliers
$503.77/5MG

Yield:869366-03-0 61%

Reaction Conditions:

Stage #1: (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 0.5 h;
Stage #2: with diethylamine in dichloromethane at 20; for 16 h;

Steps:

8.I {3-[4-Chloro-2-(2,6-difluoro-benzoyl)-phenyl]-prop-2-ynyl}-carbamic acid tert-butyl ester (3aa)

{3-[4-Chloro-2-(2,6-difluoro-benzoyl)-phenyl]-prop-2-ynyl}-carbamic acid tert-butyl ester (3aa) (5-Chloro-2-iodo-phenyl)-(2,6-difluoro-phenyl)-methanone (2aa) (5.5 g, 14.5 mmol), prop-2-ynyl-carbamic acid tert-butyl ester (2.5 g, 16 mmol), PdCl₂(PPh₃)₂(0.6 g, 0.9 mmol) and Cu(I)I (0.2 g, 0.9 mmol) were suspended in anhydrous CH₂Cl₂(50 mL) and the mixture was sparged with nitrogen for 30 min. Diethylamine (8 mL) was added and the solution was stirred at room temperature for 16 h. The solution was concentrated in vacuo and the resulting residue purified by column chromatography (silica gel, 0 to 15% EtOAc/hexanes) to afford 3aa (3.6 g, 61%) as a white solid, MS m/z=406 (M+H).

References:

US2005/256102,2005,A1 Location in patent:Page/Page column 142-143