Category: 154048-89-2

Electric Literature of 154048-89-2 ,Some common heterocyclic compound, 154048-89-2, molecular formula is C10H13IN2O2, 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.

tert-Butyl [2,4′-bipyridin]-3′-ylcarbamate. To a pressure vessel was added tert- butyl (4-iodopyridin-3-yl)carbamate (0.25g, 0.781 mmol), 2-(4,4,5,5-tetramethyl- l,3,2-dioxaborolan-2-yl)pyridine (0.176 g, 0.859 mmol) and PdC12(dppf)- CH2C12Adduct (0.032 g, 0.039 mmol). The reaction mixture was degassed and flushed with N2 (3x). Then Dioxane (5) was added and the system was degassed and flushed with N2(3x). SODIUM CARBONATE (0.781 ml, 1.562 mmol) was added and the system was degassed and flushed with N2(3x). The reaction mixture was heated to 85 C for 3h. The reaction was diluted with ethyl acetate and satd ammonium chloride. The org layer was washed with water, brine and dried over sodium sulfate. The crude product was dissolved in a small amount of dichloromethane and charged to 1 lOg silica gel cartridge which was eluted with 0- 100% ethyl acetate / hexanes over a period of 60 mins. The desired fractions were combined and dried under vacuo to give tert-butyl [2,4′-bipyridin]-3′-ylcarbamate (0.02 g, 0.074 mmol, 9.44 % yield). MS (ESI) (m/z): 272.1(M+H)+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,154048-89-2, its application will become more common.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; LUO, Guanglin; CHEN, Ling; DUBOWCHIK, Gene M.; JACUTIN-PORTE, Swanee E.; VRUDHULA, Vivekananda M.; PAN, Senliang; SIVAPRAKASAM, Prasanna; MACOR, John E.; WO2015/69594; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 154048-89-2 , The common heterocyclic compound, 154048-89-2, name is N-Boc-3-Amino-4-iodopyridine, molecular formula is C10H13IN2O2, 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.

A resealable pressure vessel was charged with tert-butyl tert-butyl (4-iodopyridin-3-yl)carbamate (1.54 g, 4.8 mmol), ((prop-2-yn-1-yloxy)methyl)benzene (0.84 g, 5.8 mmol), bis(triphenylphosphine) palladium(II) chloride (0.17g, 0.24 mmol), copper(I) iodide (0.09 g, 0.48mmol), triethylamine (15 mL, 108 mmol) and DMF (5 mL). The mixture was degassed by bubbling nitrogen through for several minutes, the flask was sealed and the reaction mixture was stirred for 7h.. The mixture was diluted with EtOAc and washed with saturated ammonium chloride (2x) and brine (1x). The organics were dried over sodium sulfate, filtered and evaporated, and the crude material purified by silica gel chromatography, eluting with 12-100% EtOAc in hexanes, affording tert-butyl (4-(3-(benzyloxy)prop-1-yn-1-yl)pyridin-3-yl)carbamate (1.6 g, 98%). 1H NMR (400MHz, CHLOROFORM-d) delta = 9.44 (s, 1H), 8.28 (d, J=4.8 Hz, 1H), 7.45 – 7.33 (m, 5H), 7.26 (d, J=4.8 Hz, 1H), 7.14 – 6.93 (m, 1H), 4.71 (s, 2H), 4.50 (s, 2H), 1.56 (s, 9H).

The synthetic route of 154048-89-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; McDonald, Ivar M.; Mate, Robert; Ng, Alicia; Park, Hyunsoo; Olson, Richard E.; Tetrahedron Letters; vol. 59; 8; (2018); p. 751 – 754;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 154048-89-2 , The common heterocyclic compound, 154048-89-2, name is N-Boc-3-Amino-4-iodopyridine, molecular formula is C10H13IN2O2, 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.

Alternate Preparation: Tert-butyl 2-((benzyloxy)methyl)-lH-pyrrolo[2,3- c]pyridine-l-carboxylate was also prepared in an alternate preparation directly from tert-butyl tert-butyl (4-iodopyridin-3-yl)carbamate: In a sealed tube was added ((prop-2-yn-l-yloxy)methyl)benzene (104 mu, 0.750 mmol) and tert-butyl (4- iodopyridin-3-yl)carbamate (200 mg, 0.625 mmol) in DMF (625 mu). To this was added PdCl2(PPh3)2 (21.93 mg, 0.031 mmol), copper(I) iodide (11.90 mg, 0.062 mmol) and TEA (1742 mu, 12.50 mmol). This reaction was then degassed for 15 minutes and then allowed to stir at 80 C sealed. After 4 hours the reaction was complete. The reaction mixture was poured into ethyl acetate and saturated ammonium chloride. The organic was collected and washed several times with ammonium chloride. The organic was then purified on the biotage eluting in 10% ethyl acetate for 10 column volumes and then 10%-40% Ethyl acetate in hexanes over 10 column volumes. The product, tert-butyl 2-((benzyloxy)methyl)-lH- pyrrolo[2,3-c]pyridine-l-carboxylate (179 mg, 85% yield) was collected as a dark yellow oil. 1H NMR (400MHz, CHLOROFORM-d) delta = 9.58 – 9.20 (m, 1H), 8.70 – 8.42 (m, 1H), 7.54 – 7.34 (m, 6H), 6.78 (s, 1H), 4.98 (d, J=1.3 Hz, 2H), 4.73 (s, 2H), 1.69 (s, 9H).

The synthetic route of 154048-89-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; MCDONALD, Ivar, M.; OLSON, Richard, E.; MATE, Robert, A.; WO2015/191401; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 154048-89-2, Adding some certain compound to certain chemical reactions, such as: 154048-89-2, name is N-Boc-3-Amino-4-iodopyridine,molecular formula is C10H13IN2O2, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 154048-89-2.

To a solution of (4-iodo-pyridin-3-yl)-carbamic acid tert-butyl ester (280 mg, 875 mumol) in DMF (4 mL) was added NaH (42.0 mg, 962 mumol, 60% dispersion in mineral oil) at 0 C. The reaction mixture was stirred at room temperature for 30 minutes. 2,2,2-Trifluoroethyl trifluoromethanesulphonate (203 mg, 126 muL, 875 mumol, CAS RN 6226-25-1) was added and the reaction stirred at room temperature for 2 hours. The reaction mixture was poured on 30 mL 10% aqueous NaHCO3 solution and 30 mL EtOAc and the layers were separated. The aqueous layer was extracted a second time with 30 mL EtOAc and the combined organic layers were washed with 30 mL brine, dried over MgSO4, filtered and concentrated under vacuum. The compound was purified by silica gel chromatography using a MPLC system (CombiFlash Companion, Isco Inc.) eluting with a gradient of n-heptane:EtOAc (100:0 to 30:70). Colorless solid (207 mg, 59%). MS (ESI): m/z=403.012 [M+H]+.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles. 154048-89-2, N-Boc-3-Amino-4-iodopyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Bissantz, Caterina; Dehmlow, Henrietta; Erickson, Shawn David; Karnachi, Prabha Saba; Kim, Kyungjin; Martin, Rainer E.; Mattei, Patrizio; Sander, Ulrike Obst; Pietranico-Cole, Sherrie Lynn; Richter, Hans; Ullmer, Christoph; US2012/232051; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem