* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
With iron; ammonium chloride In ethanol; water for 2 h; Reflux
Compound 10a was dissolved in EtOH (20 ml), and an aqueous solution of iron powder (2.5 g) and ammonium chloride (0.53 g, 10 mmol) was added and the reaction was refluxed for 2 hours. Followed by hot filter, collected filtrate spin dry. The solid was dissolved in acetone and the filtrate was collected by filtration and the solution was spin-dried to give compound 11a in 89.8percent yield.
Reference：
[1] Synthesis (Germany), 2012, vol. 44, # 16, p. 2579 - 2586
[2] Synthetic Communications, 2000, vol. 30, # 20, p. 3639 - 3644
[3] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2000, vol. 39, # 9, p. 709 - 711
[4] Patent: CN106699755, 2017, A, . Location in patent: Paragraph 0103; 0195; 0196
[5] Journal of Chemical Research, 2006, # 4, p. 223 - 224
[6] Bioorganic and Medicinal Chemistry, 2010, vol. 18, # 9, p. 3088 - 3115
[7] Chemische Berichte, 1902, vol. 35, p. 3330
[8] Chemische Berichte, 1874, vol. 7, p. 498
[9] Helvetica Chimica Acta, 1937, vol. 20, p. 691,699
[10] Journal fuer Praktische Chemie (Leipzig), 1986, vol. 328, # 4, p. 497 - 514
[11] Journal of Medicinal Chemistry, 1986, vol. 29, # 3, p. 417 - 423
[12] Arzneimittel-Forschung/Drug Research, 1999, vol. 49, # 2, p. 81 - 87
[13] Chemical Communications, 2005, # 43, p. 5438 - 5440
[14] Journal of Organic Chemistry, 2009, vol. 74, # 11, p. 4272 - 4277
[15] Journal of Medicinal Chemistry, 2012, vol. 55, # 4, p. 1559 - 1571
[16] Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 16, p. 3968 - 3973
[17] European Journal of Medicinal Chemistry, 2017, vol. 136, p. 372 - 381
2
[ 55-21-0 ]
[ 591-19-5 ]
[ 16091-26-2 ]
Yield
Reaction Conditions
Operation in experiment
92%
With copper(l) iodide; dimethylaminoacetic acid; potassium carbonate In N,N-dimethyl-formamide at 100℃; for 24 h; Schlenk technique; Inert atmosphere
General procedure: A Schlenk tube was charged with amide (1.2 mmol), aryl halide (1 mmol), CuI (0.05 or 0.1 mmol), N,N-dimethylglycine (0.1 or 0.2 mmol), and potassium carbonate (2 mmol). The tube was evacuated and backfilled with argon at room temperature. DMF (0.5 mL) was added under argon via syringe. The Schlenk tube was immersed in a preheated oil bath and the reaction mixture was stirred for the specified time at the indicated temperature. The cooled mixture was partitioned between water and ethyl acetate. The organic layer was separated and the aqueous layer was extracted with ethyl acetate.The combined organic layers were washed with brine, dried over Na2SO4, and concentrated in vacuo. The residue was purified by column chromatography on silica gel (eluting with 1:8 to 1:2 ethyl acetate/petroleum ether) to give the the desired N-aryl amides.
Chemistry
Pharmaceutical Intermediates
Inhibitors/Agonists
Material Science
For Research Only
120K+ Compounds
Competitive Price
1-2 Day Shipping
