methyl 2-(1-oxoisoindolin-2-yl)acetate synthesis
- Product Name:methyl 2-(1-oxoisoindolin-2-yl)acetate
- CAS Number:96017-03-7
- Molecular formula:C11H11NO3
- Molecular Weight:205.21
201230-82-2
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96017-03-7
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Yield:96017-03-7 89%
Reaction Conditions:
with palladium diacetate;triethylamine;triphenylphosphine in N,N-dimethyl-formamide at 50; under 750.075 Torr; for 24 h;chemoselective reaction;
Steps:
4.2. Cycloaminocarbonylation of 2-iodobenzyl bromide (1) in the presence of primary amines under atmospheric carbon monoxide pressure
General procedure: In a typical experiment Pd(OAc)2 (5.6 mg, 0.025 mmol), PPh3 (13.1 mg, 0.05 mmol), 2-iodobenzyl bromide (297 mg,1 mmol), 6 mmol of tert-butylamine (0.63 mL, 6 mmol or 2.2 mmol of amino acid methylester hydrochloride) and 0.5 mL triethylamine were dissolved in DMF (10 mL) under argon in a 100 mL three-necked flask equipped with a gas inlet, reflux condenser with a balloon at the top. The atmosphere was changed to carbon monoxide. The reaction was conducted for the given reaction time upon stirring at 50 °C and analysed by GC-MS. The mixture was then concentrated and evaporated to dryness. The residue was dissolved in chloroform (20 mL) and washed with water (20 mL). The organic phase was thoroughly washed twice with 5% HCl (20 mL), saturated NaHCO3 (20 mL), brine (20 mL), dried over Na2SO4 and concentrated to powder-like crystalline material in case of 2a-c or to a waxy residue in case of 2d,e. All compounds were subjected to column chromatography under the conditions indicated in Section 4.5.
References:
Marosv?lgyi-Haskó, Diána;Takács, Attila;Riedl, Zsuzsanna;Kollár, László [Tetrahedron,2011,vol. 67,# 5,p. 1036 - 1040] Location in patent:experimental part
5680-79-5
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96017-03-7
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96017-03-7
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$65.00/25mg