Category: 159217-89-7

Some common heterocyclic compound, 159217-89-7, name is tert-Butyl (4-iodophenyl)carbamate, molecular formula is C11H14INO2, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. Computed Properties of C11H14INO2

fert-Butyl 4-iodophenylcarbamate (prepared using the method described in Bioorganic and Med. Chem. Lett, 2000, 8, 1203; 1.77 g, 5.55 mmol) and trans-dichlorobis (triphenylphosphine) palladium (II) (195 mg, 0.28 mmol) were weighed into a flask. The flask was degassed and placed under argon, and 1,4-dioxane (30 ml) was added. The hexamethylditin (2.00 g, 6.10 mmol) was dissolved in 5 ml of 1 ,4-dioxane, and the solution was added to the mixture. The suspension was heated at 90 C for ca. 16 h. The mixture was adsorbed onto silica gel and concentrated under vacuum. The material was purified by flash chromatography on silica gel using 1% EtOAc/hexanes to give 860 mg of the desired product. NMR: 0.23 (s, 9H), 1.47 (s, 9H), 7.33 (d, 2H), 7.42 (d, 2H), 9.28 (s, IH).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 159217-89-7, its application will become more common.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2006/92599; (2006); A2;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Some common heterocyclic compound, 159217-89-7, name is tert-Butyl (4-iodophenyl)carbamate, molecular formula is C11H14INO2, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. Computed Properties of C11H14INO2

Step B [4-(t-Butoxycarbonylamino)phenyl]trimethylstannane The iodide (2.75 g; 8.62 mmol) from Step A of this Example, hexamethylditin (4.23 g; 12.91 mmol) and tetrakis(triphenylphosphine)palladium(0) were mixed together in anhydrous dioxane and subjected to a freeze-vac-thaw cycle to degas the solution and then the reaction heated to reflux under a nitrogen atmosphere for 6 h. The reaction mixture was then cooled to room temperature, poured into iced saturated brine and extracted with ether (3*250 ml). The ethereal layers were combined and washed with another portion of brine, dried over anhydrous magnesium sulfate powder and evaporated under reduced pressure to leave an orange mobile liquid. Chromatography of the liquid on silica gel using an eluant consisting of ether and hexanes in the ratio 1:19 v/v afforded 1.75 g (ca. 57%) of a material that was [4-(t-butoxycarbonylamino)phenyl]trimethylstannane that contained traces of the starting material. 1 H NMR (200 MHz, CDCl3): 0.23 (s, 9H) 1.47 (s, 9H) 6.45 (s, 1H) 7.25-7.40 (ABq, 4H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 159217-89-7, its application will become more common.

Reference:
Patent; Merck & Co., Inc.; US5726319; (1998); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Application of 159217-89-7, A common heterocyclic compound, 159217-89-7, name is tert-Butyl (4-iodophenyl)carbamate, molecular formula is C11H14INO2, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

5 g (15,7 mmol) N-tert-Butyloxycarbonyl-4-iodanilin (BOC-geschuetztes 4-lodanilin) in 30 ml Toluol wurden bei Raumtemperatur mit einer Spatelspitze 4-Dimethylaminopyridin als Katalysator und 5,02 g (23,0 mmol) Di-tertbutyldicarbonat (BOC-Anhydrid) versetzt. Man liessueber Nacht ruehren, verduennte mit 30 ml Dichlormethan, wusch mit 20 ml 5 %iger Salzsaeure, trennte die Phasen und engte die organische Phase bis zur Trockene ein. Der Rueckstand wurde im Hochvakuum von Loesungsmittelresten befreit. Man erhielt das zweifach BOCgeschuetzte 4-lodanilin in 4,41 g (10,5 mmol, 67 %) Ausbeute. Die gesamte Menge wurde in 25 ml THF geloest und zu einer auf -78C gekuehlten Loesung von Lithiumtributylmagnesat in THF/Hexan (ca. 44 ml, 12,6 mmol) getropft (hergestellt aus Butylmagnesiumbromid-Loesung in THF und Butyllithium-Loesung in Hexan bei 0 C). Nach 40 min Nachruehren wurden 3,27 g (31,5 mmol) Trimethylborat langsam zugetropft. Man ruehrte noch 30 min bei -78C nach und liess dann langsam auf 0C erwaermen. Zur Hydrolyse wurden 70 ml 2 N methanolischer Chlorwasserstoff zugegeben und 7 h geruehrt. Zur Isolierung des Produkts gab man das Gemisch in 250 ml Wasser und 250 ml Toluol, extrahierte und trennte die Phasen. Die Toluolphase wurde eingeengt und das Produkt aus Methanol umkristallisiert. Man erhielt 0,64 g (3,7 mmol, 35 %) des 4-Anilinboronsaeure-Hydrochlorids; zusaetzlich war durch Protodeborierung eine nicht bestimmte Menge Anilin entstanden (Ausbeute ueber beide Stufen 23,5 %).

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; Clariant GmbH; EP1479686; (2004); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com