N-PROPARGYLPHTHALIMIDE synthesis
- Product Name:N-PROPARGYLPHTHALIMIDE
- CAS Number:7223-50-9
- Molecular formula:C11H7NO2
- Molecular Weight:185.18
1074-82-4
106-96-7
7223-50-9
General procedure for the synthesis of N-propargyl phthalimide from phthalimide potassium salt and 3-bromopropargyl: 8.4 mmol of 3-bromopropargyl and 8.4 mmol of phthalimide potassium salt were dissolved in 10 mL of N,N-dimethylformamide. Subsequently, 0.2 g of manganese dioxide solid was added as a catalyst. The reaction mixture was stirred at 28°C for 2 hours. Upon completion of the reaction, the mixture was diluted by adding 100 mL of ethyl acetate to the mixture, followed by washing with water to collect the organic layer. The organic layer was further washed with saturated aqueous sodium chloride solution and dried with anhydrous sodium sulfate. The dried organic phase was separated and purified by column chromatography with the eluent being a solvent mixture of petroleum ether and ethyl acetate (5:1, v/v) to obtain pure N-propargyl phthalimide.
1074-82-4
498 suppliers
$5.00/25g
106-96-7
343 suppliers
$30.00/25g
7223-50-9
100 suppliers
$40.00/5g
Yield:7223-50-9 98%
Reaction Conditions:
in N,N-dimethyl-formamide at 25; for 16 h;Inert atmosphere;
Steps:
2 - Prop-2-ynylisoindoline-1,3-dione (Intermediate ASN)
A mixture of (1, 3-dioxoisoindolin-2-yl)potassium (3.00 g, 16.2 mmol) and 3-bromoprop-1-yne (2.89 g, 24.3 mmol) in DMF (20 mL) was stirred at 25 °C for 16 hours. On completion, the mixture was diluted in water (80 mL), and a large amount of yellow solid precipitated from the solution. The mixture was filtered and the filter cake was collected and dried in vacuo to afford the title compound (2.94 g, 98% yield) as a light solid. LC-MS (ESI+) m/z 186.0 (M+H)+.
References:
KYMERA THERAPEUTICS, INC.;MAINOLFI, Nello;JI, Nan;KLUGE, Arthur F.;WEISS, Matthew M.;ZHANG, Yi;ZHENG, Xiaozhang WO2020/113233, 2020, A1 Location in patent:Paragraph 00962; 004829
