Home Cart Sign in  
HazMat Fee +

There will be a HazMat fee per item when shipping a dangerous goods. The HazMat fee will be charged to your UPS/DHL/FedEx collect account or added to the invoice unless the package is shipped via Ground service. Ship by air in Excepted Quantity (each bottle), which is up to 1g/1mL for class 6.1 packing group I or II, and up to 25g/25ml for all other HazMat items.

Type HazMat fee for 500 gram (Estimated)
Excepted Quantity USD 0.00
Limited Quantity USD 15-60
Inaccessible (Haz class 6.1), Domestic USD 80+
Inaccessible (Haz class 6.1), International USD 150+
Accessible (Haz class 3, 4, 5 or 8), Domestic USD 100+
Accessible (Haz class 3, 4, 5 or 8), International USD 200+
Chemical Structure| 180691-65-0 Chemical Structure| 180691-65-0

Structure of 180691-65-0

Chemical Structure| 180691-65-0

*Storage: {[sel_prStorage]}

*Shipping: {[sel_prShipping]}

,{[proInfo.pro_purity]}

4.5 *For Research Use Only !

{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]} Purity: {[proInfo.pro_purity]}

Change View

Size Price VIP Price

US Stock

Global Stock

In Stock
{[ item.pr_size ]} Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price, item.vip_usd) ]}

US Stock: ship in 0-1 business day
Global Stock: ship in 5-7 days

  • {[ item.pr_size ]}

In Stock

- +

Please Login or Create an Account to: See VIP prices and availability

US Stock: ship in 0-1 business day
Global Stock: ship in 2 weeks

  • 1-2 Day Shipping
  • High Quality
  • Technical Support
Product Citations

Alternative Products

Product Details of [ 180691-65-0 ]

CAS No. :180691-65-0
Formula : C11H16F3NO5S
M.W : 331.31
SMILES Code : O=C(N1CCC=C(OS(=O)(C(F)(F)F)=O)C1)OC(C)(C)C
MDL No. :MFCD26391806

Safety of [ 180691-65-0 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H302-H312-H332-H335-H314
Precautionary Statements:P260-P264-P270-P271-P280-P301+P330+P331-P302+P352-P303+P361+P353-P304+P340-P305+P351+P338-P310-P363-P403+P233-P405-P501
Class:8
UN#:1760
Packing Group:

Application In Synthesis of [ 180691-65-0 ]

* 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.

  • Downstream synthetic route of [ 180691-65-0 ]

[ 180691-65-0 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 180691-65-0 ]
  • [ 73183-34-3 ]
  • [ 885693-20-9 ]
YieldReaction ConditionsOperation in experiment
71% With 1,1'-bis-(diphenylphosphino)ferrocene; potassium acetate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In 1,4-dioxane; at 80℃; for 16h; PdCl2dppf (0.16 g, 0.22 mmol), KOAc (2.18 g, 22.2 mmol), 4,4,5,5,4',4',5',5'- octamethyl-[2,2']bi[[l,3,2]dioxaborolanyl] (2.07 g, 8.13 mmol), and dppf (0.12 g, 0.22 mmol) were placed in a round-bottomed flask, and the flask was flushed with Ar. A degassed solution of 5-trifluoromethanesulfonyloxy-3,6-dihydro-2H-pyridine-l-carboxylic acid tert-butyl ester (as prepared in the previous step, 2.45 g, 7.40 mmol) in dioxane (70 mL) was added to the flask and heated to 80 0C for 16 h. The mixture was filtered through a glass-fritted funnel to remove the solid KOAc, and the filtrate was concentrated in vacuo. Silica gel chromatography (5 percent EtOAc in hexanes) afforded the title compound (1.62 g, 71 percent) as a colorless oil. 1H-NMR (CDCl3; 400 MHz): delta 6.69-6.60 (m, IH), 3.98 (br s, 2H), 3.49-3.42 (m, 2H), 2.24-2.16 (m, 2H), 1.47 (s, 9H), 1.27 (s, 12H). LC-MS (ESI, m/z): Calcd. for Ci8H28BNO4 310.2 (M+H), found 311.0.
71% With potassium acetate;1,1'-bis-(diphenylphosphino)ferrocene; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In 1,4-dioxane; at 80℃; for 16h; PdCl2dppf (0.16 g, 0.22 mmol), KOAc (2.18 g, 22.2 mmol), 4,4,5,5,4',4',5',5'-octamethyl-[2,2']bi[[1,3,2]dioxaborolanyl] (2.07 g, 8.13 mmol), and dppf(0.12 g, 0.22 mmol) were placed in a round-bottomed flask, and the flask was flushed with Ar. A degassed solution of 5-trifluoromethanesulfonyloxy-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester (as prepared in the previous step, 2.45 g, 7.40 mmol) in dioxane (70 mL) was added to the flask and heated to 80° C. for 16 h. The mixture was filtered through a glass-fritted funnel to remove the solid KOAc, and the filtrate was concentrated in vacuo. Silica gel chromatography (5percent EtOAc in hexanes) afforded the title compound (1.62 g, 71percent) as a colorless oil. 1H-NMR (CDCl3; 400 MHz): delta 6.69-6.60 (m, 1H), 3.98 (br s, 2H), 3.49-3.42 (m, 2H), 2.24-2.16 (m, 2H), 1.47 (s, 12H). LC-MS (ESI, m/z): Calcd. for C18H28BNO4 310.2 (M+H), found 311.0.
71% With potassium acetate;1,1'-bis-(diphenylphosphino)ferrocene; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In 1,4-dioxane; at 80℃; for 16h; b) 5-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester PdCl2dppf (0.16 g, 0.22 mmol), KOAc (2.18 g, 22.2 mmol), 4,4,5,5,4',4',5',5'-octamethyl-[2,2']bi[[1,3,2]dioxaborolanyl] (2.07 g, 8.13 mmol), and dppf (0.12 g, 0.22 mmol) were placed in a round-bottomed flask, and the flask was flushed with Ar. A degassed solution of 5-trifluoromethanesulfonyloxy-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester (as prepared in the previous step, 2.45 g, 7.40 mmol) in dioxane (70 mL) was added to the flask and heated to 80° C. for 16 h. The mixture was filtered through a glass-fritted funnel to remove the solid KOAc, and the filtrate was concentrated in vacuo. Silica gel chromatography (5percent EtOAc in hexanes) afforded the title compound (1.62 g, 71percent) as a colorless oil. 1H-NMR (CDCl3; 400 MHz): delta 6.69-6.60 (m, 1H), 3.98 (br s, 2H), 3.49-3.42 (m, 2H), 2.24-2.16 (m, 2H), 1.47 (s, 9H), 1.27 (s, 12H). LC-MS (ESI, m/z): Calcd. for C18H28BNO4 310.2 (M+H). found 311.0.
71% With 1,1'-bis(diphenylphosphino)ferrocene; potassium acetate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In 1,4-dioxane; at 80℃; for 16h; PdCl2dppf (0.16 g, 0.22 mmol), KOAc (2.18 g, 22.2 mmol), 4,4,5,5,4',4',5',5'- octamethyl-[2,2']bi[[l,3,2]dioxaborolanyl] (2.07 g, 8.13 mmol), and dppf (0.12 g, 0.22 mmol) were placed in a round-bottomed flask, and the flask was flushed with Ar. A degassed solution of 5-trifluoromethanesulfonyloxy-3,6-dihydro-2H-pyridine-l- carboxylic acid tert-butyl ester (as prepared in the previous step, 2.45 g, 7.40 mmol) in dioxane (70 mL) was added to the flask and heated to 80 0C for 16 h. The mixture was filtered through a glass-fritted funnel to remove the solid KOAc, and the filtrate was concentrated in vacuo. Silica gel chromatography (5 percent EtOAc in hexanes) afforded the title compound (1.62 g, 71 percent) as a colorless oil. 1H-NMR (CDCl3; 400 MHz): delta 6.69-6.60 (m, IH), 3.98 (br s, 2H), 3.49-3.42 (m, 2H), 2.24-2.16 (m, 2H), 1.47 (s, 9H), 1.27 (s, 12H). LC-MS (ESI, m/z): Calcd. for C18H28BNO4 310.2 (M+H), found 311.0.
70% With 1,1'-bis-(diphenylphosphino)ferrocene; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In 1,4-dioxane; at 80℃; for 18h;Inert atmosphere; Step 2 To a degassed solution of 5-trifluoromethanesulfonyloxy-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester (340 mg, 1.0 mmol, 1 eq) in dioxane (10 mL) was added bis-(pinacolato)-diboron (287 mg, 1.1 mmol, 1.1 eq), potassium acetate (302 mg, 3.0 mmol, 3 eq), 1,1'-bis(diphenylphosphino)ferrocene (17 mg, 0.03 mmol, 0.03 eq) and dichloro[1,1'-bis(diphenylphosphino)ferrocene]palladium) (23 mg, 0.03 mmol, 0.03 eq) were added. The mixture was stirred at 80° C. for 18 h. After cooling down, the mixture was filtered and the filtrate was concentrated and purified by flash chromatography using cyclohexane and ethyl acetate (100/0 to 96/4) to afford the corresponding boronic ester (225 mg, 70percent yield).
64% With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate; In 1,4-dioxane; at 80℃;Inert atmosphere; To a solution of tert-butyl 3-(trifluoromethylsulfonyloxy)-5,6-dihydropyridine- l(2H)- carboxylate (503-2) (1.4 g, 4.3 mmol), BPin ( 1.3 g, 5.1 mmol) and KOAc (1.26 g, 12.9 mmol) in dioxane (10 mL) was added Pd(dppf)Cl2.DCM (351 mg, 0.43 mmol). The resulting mixture was purged with N2 X 3 and heated to 80 °C overnight. The solvent was removed in vacuo and the residue was purified by column chromatography (silica gel, 0 to 10percent EA in PE) to give tert-butyl 3-(4,4,5,5-tetramethyl- 1,3,2- dioxaborolan-2-yl)-5,6-dihydropyridine-l(2H)-carboxylate (503-3) (850 mg, 64percent) as a yellow oil.
42% With potassium acetate;1,1'-bis-(diphenylphosphino)ferrocene; [1,1?-bis(diphenylphosphino)ferrocene]dichloropalladium(II)-acetone complex; In 1,4-dioxane; at 80℃; for 12h; To a high pressure vessel was added 5-trifluoromethanesulfonyloxy-3,6- dihydro-2H-pyridine- l-carboxylic acid tert-butyl ester (1.0 g, 3.0 mmol), dichloro[l ,l '- bis(diphenylphosphino)ferrocene]palladium (II) acetone adduct (0.2 g, 0.3 mmol), Iota , - bis(diphenylphosphino)ferrocene (0.2 g, 0.3 mmol), bis(pinacolato)diboron (0.84 g, 3.3 mmol) and K2OAc (0.89 g, 9.0 mmol) in 1 ,4-dioxane (7 mL, 90 mmol). The reaction was heated for 12 h at 80 °C. After cooling to RT, the mixture was diluted with EtOAc, the organic phase was concentrated in vacuo, and the residue purified by column chromatography to afford the named compound (42percent). .H NMR (CDC13, 400 MHz): delta 6.57 (br. s., 1H), 3.91 (br. s., 2H), 3.39 (t, J = 5.81 Hz, 2H), 2.13 (br. s., 2H), 1.39-1.41 (m, 9H), 1.19 (s, 12H).
41% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In N,N-dimethyl-formamide; at 85℃; for 4h;Inert atmosphere; A mixture of tert-butyl 5-(((trifluoromethyl)sulfonyl)oxy)-3,6-dihydropyridine-1(2H)-carboxylate (3.5 g, 14.5 mmol), Pd(dppf)Cl2 (0.38 g, 0.53 mmol), bis(pinacolato)diboron (3.9 g, 15.8 mmol), and KOAc (3.1 g, 31.5 mmol) in anhydrous DMF was degassed and purged with nitrogen three times. The mixture was heated at 85° C. for 4 h. After cooling down to room temperature, the reaction was diluted with ethyl acetate, filtered, and concentrated. The crude residue was purified by silica gel column chromatography to afford tert-butyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,6-dihydropyridine-1(2H)-carboxylate (1.4 g, 41percent) as a colorless oil.
With potassium acetate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In 1,4-dioxane; at 80℃; To a 25 mL round bottom flask charged with bis(pinacolato)diboron (1.50 g, 6 mmol), potassium acetate (1.5 g, 15 mmol), Pd(dppf)Cl2 (408 mg, 0.5 mmol) and DPPF (277 mg, 0.5 mmol). Compound 195 (1.55 g, 5.0 mmol) in dioxane 20 mL) was added to the above mixture. The mixture was degassed thoroughly and placed under argon. This resulting mixture was then heated at 80° C. for overnight, diluted with EtOAc (40 mL) and filtered through celite. After concentration, the residue was purified with column chromatography (silica gel, Hexane/EtOAc=60/40) to give the product (832 mg) as an oil. HPLC-MS tR=2.41 min (UV254 nm), mass calculated for formula C16H28BNO4, 309.2; observed MH+-t-Bu (LCMS) 254.2(m/z).
With potassium acetate; In 1,4-dioxane; Preparation 5: tert-butyl 5-(3H-pyrroIo[3,2-fJ[l,7]naphthyridin-9-yl)-3,6-dihydro-2H- pyridine-l-carboxylate (36) The compound 36 is prepared according to the procedure described in patent applications WO 2007/146838 and WO 2010/059771
With potassium acetate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In 1,4-dioxane; at 80℃;Inert atmosphere; 5-(4,4,5,5-Tetramethyl-1 ,3,2-dioxaborolan-2-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester[370] A mixture of Bis(pinacolato)diboron (0.864 g, 3.40 mmol), (1 ,1'-bis-(diphenyl- phosphino)ferrocene)palladium (0.29 g, 0.39 mmol), potassium acetate (0.642 g, 6.54 mmol) and 5-trifluoromethanesulfonyloxy-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester(0.600 g, 1.81 mmol) in 1 ,4-dioxane (20 ml.) was degassed and refilled with N2 three times.The resulting material was stirred at 80 °C for overnight. The reaction mixture was filtrated through a celite pad, concentrated in vacuo and purified by silica gel (Hexanes: EtOAc = 9:1 , v:v) to afford the desired product. 1H NMR (400 MHz, CDCI3): delta = 1.38 (s, 9 H), 2.01-2.19 (m,2 H), 3.28-3.41 (m, 2 H), 3.89 (d, J = 2.23 Hz, 2 H), 6.55 (br. s., 1 H).

  • 2
  • [ 180691-65-0 ]
  • [ 885693-20-9 ]
YieldReaction ConditionsOperation in experiment
A round-bottomed flask was charged with tert-butyl 5-(((trifluoromethyl)sulfonyl)oxy)-3,6-dihydropyridine-1(2H)-carboxylate (2.5 g, 7.55 mmol), bis(pinacolato)diboron (2.88 g, 11.33 mmol), Potassium acetate (2.22 g, 22.7 mmol), and PdCl2(dppf) (276 mg, 0.38 mmol). After degassed, dioxane (40 mL) was added. The reaction mixture was heated to 90° C. for 3 h. After the reaction was completed, the mixture was cooled to rt. 40 mL of EtOAc was added, and the reaction mixture was washed with water for 3 times. The organic phase was dried over anhydrous sodium sulphate and then concentrated. The residue was purified by flash chromatography (1:8:12 EtOAc/DCM/Hexane). 1.5 g (64.3percent) of tert-butyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,6-dihydropyridine-1(2H)-carboxylate was obtained as a solid.
 

Historical Records

Technical Information

Categories