2-CHLORO-N-CYCLOHEXYLNICOTINAMIDE synthesis
- Product Name:2-CHLORO-N-CYCLOHEXYLNICOTINAMIDE
- CAS Number:57841-70-0
- Molecular formula:C12H15ClN2O
- Molecular Weight:238.71
10366-35-5
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$9.00/10g
98-89-5
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$13.00/25g
57841-70-0
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$22.30/1g
Yield:57841-70-0 70%
Reaction Conditions:
with copper(I) thiophene-2-carboxylate;(4,4'-di-tert-butyl-2,2'-dipyridyl)-bis-(5-methyl-2-(4-fluorophenyl)pyridine(-1H))-iridium(III) hexafluorophosphate;N,N,N′,N′-tetramethyl-N″-tert-butylguanidine;bathophenanthroline;iodomesitylene diacetate in 1,4-dioxane at 20; for 1 h;Inert atmosphere;Irradiation;regioselective reaction;
Steps:
Procedure for decarboxylative sp3 C-N couplings
General procedure: To a 20 ml or 40 ml viale quipped with a stir bar was added photocatalyst, nitrogen nucleophile, iodomesitylene dicarboxylate, copper salt, and ligand. Dioxane was added followed by addition of the base. The solution was sonicated for 1-3 min until it became homogeneous. Next, the solution was degassed by sparging with nitrogen for 5-10 min before sealing with Parafilm. The reaction was stirred and irradiated using two 34-W blue LED lamps (3 cm away, with cooling fan to keep the reaction at room temperature) for 1 h. The reaction mixture was removed from the light, cooled to ambient temperature, diluted with water (15 ml) and ethyl acetate (25 ml), and the aqueous layer was extracted with ethyl acetate (3 × 25 ml). The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated. The residue was purified by flash chromatography on silica gel to afford the desired decarboxylative C-N coupling product. For aniline substrates, a solution of these nitrogen nucleophiles in dioxane was used; additionally, if the iodomesitylene dicarboxylate is a liquid, its solution in dioxane was used.
References:
Liang, Yufan;Zhang, Xiaheng;MacMillan, David W. C. [Nature,2018,vol. 559,# 7712,p. 83 - 88]
49609-84-9
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108-91-8
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57841-70-0
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$22.30/1g
2942-59-8
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57841-70-0
25 suppliers
$22.30/1g