Category: 173979-01-6

Analyzing the synthesis route of 173979-01-6

173979-01-6 4-(Tributylstannyl)thiazole 2763258, athiazole compound, is more and more widely used in various fields.

173979-01-6, 4-(Tributylstannyl)thiazole is a thiazole compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a solution of ethyl 3-(2-(6-chioro-3-cvano- 4-methyipyridin-2-yi)-5-fluoro- I ,2,3,4-tetrahydroisoquinolin-6-yI)propanoate (50 mg, 0.124 mrnol) and 4-(tributylstannyi)thiazoie (51.2 mg, 0.137 mrnol) in dioxane (3 ml) was added (i2 XPhos (979mg. 0.012 mmol). The mixture was stirred at 110 c for 12 h, then quenched with 10% aqueous KF (10 ml), filtered and extracted with ethyl acetate (8 niL x 3). The organic layers were combined and washed with water (15 mL), brine (10 mL), dried over Na2SO4,filtered and concentrated under reduced pressure to afford the title compound, which was used directly without further purification., 173979-01-6

173979-01-6 4-(Tributylstannyl)thiazole 2763258, athiazole compound, is more and more widely used in various fields.

Reference£º
Patent; MERCK SHARP & DOHME CORP.; ADAMS, Gregory, L.; COX, Jason, M.; DEBENHAM, John, S.; EDMONDSON, Scott; GILBERT, Eric, J.; GUO, Yan; JIANG, Yu; JOSIEN, Hubert; KIM, Hyunjin, M.; LAN, Ping; MIAO, Shouwu; PLUMMER, Christopher, W.; RAJAGOPALAN, Murali; SHAH, Unmesh; SUN, Zhongxiang; TRUONG, Quang, T.; UJJAINWALLA, Feroze; VELAZQUEZ, Francisco; VENKATRAMAN, Srikanth; SUZUKI, Takao; WANG, Nengxue; (182 pag.)WO2017/205193; (2017); A1;,
Thiazole | C3H3NS – PubChem
Thiazole | chemical compound | Britannica

New learning discoveries about 173979-01-6

173979-01-6, The synthetic route of 173979-01-6 has been constantly updated, and we look forward to future research findings.

173979-01-6, 4-(Tributylstannyl)thiazole is a thiazole compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Example 63 (3-Chloro-5-thiazol-4-yl-phenyl)-(1 H-imidazol-2-yl)-methanoneA solution of Example 53 (50 mg, 0.15 mmol) in 1 ,4-dioxane (3 ml_) was stirred in a microwave reaction tube. 4-Tributylstannanyl-thiazole (62 mg, 0.165 mmol) followed by Pd(PPh3)4 (10 mg, 8.6 mumol) was added to the stirred mixture. The tube was sealed and the reaction was heated at 1200C for 30 mins. The mixture was then diluted with EtOAc (20 ml.) and washed with brine. The organic phase was then dried over Na2SO4, filtered and the solvent evaporated. The crude was triturated in dichloromethane and the collected precipitate was purified further by SiO2 chromatography (Hexanes/ EtOAc; 9:1 to 2:1 ) to give the title compound as a beige solid (10 mg, 23%). MS(ESI) m/z 289.9 (M+H)+. 1H NMR (400 MHz, DMSO-d6): 13.62 (1 H, s), 9.28 (1 H, d), 8.97 (1 H, t), 8.58 (1 H, t), 8.46 (1 H, d), 8.34 (1 H, t), 7.58 (1 H, s), 7.39 (1 H, s).

173979-01-6, The synthetic route of 173979-01-6 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; NOVARTIS AG; ASTEX THERAPEUTICS LIMITED; HOWARD, Steven; MORTENSON, Paul Neil; HISCOCK, Steven Douglas; WOOLFORD, Alison Jo-Anne; WOODHEAD, Andrew James; CHESSARI, Gianni; O’REILLY, Marc; CONGREVE, Miles Stuart; DAGOSTIN, Claudio; CHO, Young Shin; YANG, Fan; CHEN, Christine Hiu-Tung; BRAIN, Christopher Thomas; LAGU, Bharat; WANG, Yaping; KIM, Sunkyu; GRIALDES, John; LUZZIO, Michael Joseph; PEREZ, Lawrence Blas; WO2010/125402; (2010); A1;,
Thiazole | C3H3NS – PubChem
Thiazole | chemical compound | Britannica

Analyzing the synthesis route of 173979-01-6

173979-01-6, 173979-01-6 4-(Tributylstannyl)thiazole 2763258, athiazole compound, is more and more widely used in various fields.

173979-01-6, 4-(Tributylstannyl)thiazole is a thiazole compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

In a dried microwave tube were dissolved tert-butyl [4-(5-hydroxy-8-iodo-3- phenyl-l,6-naphthyridin-2-yl)benzyl] carbamate (10-1) (100 mg, 0.18 mmol) and 4- (tributylstannyl)-l,3-thiazole (160 mg, 0.43 mmol) in THF (2 mL). N2 gas was then bubbled through the solution for 5 minutes before adding Tetrakis (21 mg, 0.018 mmol). N2 gas was bubbled through the mixture for another 5 minutes and the mixture was then heated to dryness at 1000C on a heating block overnight. The resulting residue was taken up in DMF, treated with QuadraPure TU resin for 30 minutes and filtered. The mixture was purified by reverse phase HPLC to give tert-butyl {4-[5-hydroxy-3-phenyl-8-(l,3-thiazol-4-yl)-l,6-naphthyridin-2- yljbenzyl} carbamate (11-1) as an orange residue. MS calculated M+H: 511.6; found 511.1

173979-01-6, 173979-01-6 4-(Tributylstannyl)thiazole 2763258, athiazole compound, is more and more widely used in various fields.

Reference£º
Patent; MERCK SHARP &; DOHME CORP.; BANYU PHARMACEUTICAL CO., LTD.; ARMSTRONG, Donna, J.; GOTO, Yasuhiro; HASHIHAYATA, Takashi; KATO, Tetsuya; KELLY, Michael, J., III; LAYTON, Mark, E.; LINDSLEY, Craig, W.; OGINO, Yoshio; ONOZAKI, Yu; RODZINAK, Kevin, J.; ROSSI, Michael, A.; SANDERSON, Philip, E.; WANG, Jiabing; YAROSCHAK, Melissa, M.; WO2010/88177; (2010); A1;,
Thiazole | C3H3NS – PubChem
Thiazole | chemical compound | Britannica

Downstream synthetic route of 173979-01-6

173979-01-6, The synthetic route of 173979-01-6 has been constantly updated, and we look forward to future research findings.

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.173979-01-6,4-(Tributylstannyl)thiazole,as a common compound, the synthetic route is as follows.

5-(4-Ethyl-5-(3-fluoro-4-(1,3-thiazol-4-yl)phenyl)-3-trifluoromethyl-1H-pyrazol-1-yl)-2-pyridinesulfonamide (Step 5) A mixture of 5-(5-(4-bromo-3-fluorophenyl)-4-ethyl-3-trifluoromethyl-1H-pyrazol-1-yl)-2-pyridines ulfonamide (450 mg, 0.912 mmol), 4-tributylstannyl-1,3-thiazol (410 mg, 1.095 mmol), tetrakis(triphenylphosphine)palladium (105 mg, 0.091 mmol), lithium chloride (97 mg, 2.281 mmol) in 1,4-dioxane (11 ml) was stirred at reflux for 17 h. After cooling, the mixture was diluted with ethyl acetate, washed with water. The organic layer was dried (MgSO4) and concentrated. This was purified on silica gel eluding with ethyl acetate/hexane (1:3/1:2) to afford 350 mg (77.1%) of the titled compound as a yellow solid. 1H-NMR (CDCl3) delta: 8.91-8.90 (1H, m), 8.61-8.60 (1H, m), 8.39-8.33 (1H, m), 7.97-7.92 (2H, m), 7.85-7.80 (1H, m), 7.14-7.05 (2H, m), 5.28 (2H, br.s), 2.61 (2H, q, J=7.6 Hz), 1.16 (3H, t, J=7.6 Hz) IR(KBr)v: 1470, 1448, 1354, 1292, 1178, 1157, 1128, 1076 cm-1 mp: 182-185 C.

173979-01-6, The synthetic route of 173979-01-6 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; PFIZER INC.; US2003/144280; (2003); A1;,
Thiazole | C3H3NS – PubChem
Thiazole | chemical compound | Britannica

New learning discoveries about 173979-01-6

The synthetic route of 173979-01-6 has been constantly updated, and we look forward to future research findings.

173979-01-6, 4-(Tributylstannyl)thiazole is a thiazole compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

2-(l-(phenylsulfonyl)-5-(l , 4-dioxaspiro[4.5]decan-8-yl)-lH-pyrrolo[2, 3- b] pyridin-3-yl)thiazole (IIb-87) – an alternative method of preparation(IXb-23) (IIb-87)Iodide (IXb-23) (100 mg, 0.19 mmol) and 2-(tributylstannyl)thiazole (107 mg, 0.29 mmol), tri-O-tolylphosphine (7 mg, 0.02 mmol), dichlorobis(acetonitrile)palladium(II) (3 mg, 0.01 mmol) and toluene (3 mL) were reacted for 5 h at 120 0C (oil bath) in a sealed reaction vessel using the general procedure B for the Stille reaction. The reaction mixture was filtered, concentrated and purified by LCMS (column LUNA 10 mu C 18(2) 00G-4253- VO 250×50 mm) using water – acetonitrile (0.1% AcOH) as eluent (in gradient; flow 80 mL/min) to give (IIb-87) (42.2 mg, 46%) as a white solid. 1H NMR (400 MHz, CDCl3) delta 1.57 – 1.64 (m, 2H), 1.68 – 1.76 (m, 2H), 1.86-1.91 (m, 4H), 2.70 – 2.78 (m, IH), 3.99 (s, 4H), 7.33 (d, J = 3.3 Hz, IH), 7.48-7.52 (m, 2H), 7.60 (tt, J = 1.5, 7.4 Hz, IH), 7.89 (d. J = 3.3 Hz, IH), 8.23 (s, IH), 8.24 – 8.26 (m, 2H), 8.39 (d, J= 2.1 Hz, IH), 8.45 (d, J= 2.1 Hz, IH).; Procedure B involving (IX) (IX) (H)To a stirred solution of (IX) (0.5 mmol) in toluene (2.3 rnL) was added dichlorobis(acetonitrile)palladium (II) (12 mg, 0.05 mmol), tri-o-tolylphosphine (28 mg, 0.09 mmol) and the relevant stannane (V) (0.6 mmol). The reaction was heated to reflux (bath temperature HO0C) and the reaction monitored by TLC. When starting material was no longer present (2 – 6 hrs), the reaction mixture was poured onto saturated aqueous NaHCO3 (60 mL) and extracted with AcOEt (2 x 60 mL). The combined organic solutions were dried (MgSO4) and concentrated to give an oil which was purified using SGC and CH2Cl2 :hexane: AcOEt as eluent (gradient from CH2Cl2 :hexane: AcOEt= 1 : 1 :0 to 9:9:2, v/v) to afford the protected 3-thiazolyl 7-azaindole (II). Yield 25 – 80%.

The synthetic route of 173979-01-6 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; EISAI LONDON RESEARCH LABORATORIES LIMITED; WO2008/95943; (2008); A1;,
Thiazole | C3H3NS – PubChem
Thiazole | chemical compound | Britannica

New learning discoveries about 173979-01-6

The synthetic route of 173979-01-6 has been constantly updated, and we look forward to future research findings.

173979-01-6, 4-(Tributylstannyl)thiazole is a thiazole compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

(R)-7-(4-bromo-lH-imidazol-l-yl)-5-cyclopentyl-4-ethyl-4,5-dihydro- [l,2,4]triazolo[4,3-f]pteridine (Example 93), 4-(tributylstannyl)thiazole (1 eq, seeExample 693) and Pd(PPli3)4 (0.1 eq) are dissolved in DMF in a screw cap vial and a stream of nitrogen is bubbled through the mixture for 2 minutes. The vial is sealed and the resulting solution is stirred at 100 C for 19 h. The reaction mixture is diluted with brine, extracted with EtOAc, dried with Na2S04 then purified by flash chromatography with a silica gel column by eluting with a mixture of Hexane:EtOAc and then further purified by preparative HPLC to give the title compound.

The synthetic route of 173979-01-6 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; ELAN PHARMACEUTICALS, INC.; NEITZ, R., Jeffrey; TROUNG, Anh, P.; GALEMMO, Robert, A.; YE, Xiaocong, Michael; SEALY, Jennifer; ADLER, Marc; BOWERS, Simeon; BEROZA, Paul; ANDERSON, John, P.; AUBELE, Danielle, L.; ARTIS, Dean, Richard; HOM, Roy, K.; ZHU, Yong-liang; WO2012/48129; (2012); A2;,
Thiazole | C3H3NS – PubChem
Thiazole | chemical compound | Britannica