TERT-BUTYL 5-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-3,6-DIHYDROPYRIDINE-1(2H)-CARBOXYLATE Chemical Properties

Melting point:

105 °C

Boiling point:

348.0±52.0 °C(Predicted)

Density 

1.05

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

form 

solid

pka

-1.17±0.40(Predicted)

color 

White to Light yellow

InChI

InChI=1S/C16H28BNO4/c1-14(2,3)20-13(19)18-10-8-9-12(11-18)17-21-15(4,5)16(6,7)22-17/h9H,8,10-11H2,1-7H3

InChIKey

KEEIJBAOTMNSEN-UHFFFAOYSA-N

SMILES

C1N(C(OC(C)(C)C)=O)CC(B2OC(C)(C)C(C)(C)O2)=CC1

Safety Information

WGK Germany 

3

HS Code 

2933399990

TERT-BUTYL 5-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-3,6-DIHYDROPYRIDINE-1(2H)-CARBOXYLATE Usage And Synthesis

Uses

tert-Butyl 5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-3,4-dihydropyridine-1(2H)-carboxylate is used as a reactant in the synthesis of phosphatidylinositol 3-kinase inhibitors.

Synthesis

General procedure: PdCl2 (dppf) (0.16 g, 0.22 mmol), KOAc (2.18 g, 22.2 mmol), bis(pinacolato)diboron (2.07 g, 8.13 mmol), and dppf (0.12 g, 0.22 mmol) were added to a round-bottomed flask and the flask flushed with argon. A solution of degassed tert-butyl 5-(((trifluoromethyl)sulfonyl)oxy)-3,6-dihydropyridine-1(2H)-carboxylate (2.45 g, 7.40 mmol) in dioxane (70 mL) was added to the flask. The reaction mixture was heated to 80 °C and stirred for 16 hours. After completion of the reaction, it was filtered through a glass sintered funnel to remove the solid KOAc and the filtrate was concentrated under reduced pressure. Purification by silica gel column chromatography (eluent: 5% EtOAc in hexane solution) afforded tert-butyl 3-boronic acid pinacol esteryl-5,6-dihydropyridine-1(2H)-carboxylate (1.62 g, 71%) as a colorless oil.1H NMR (400 MHz, CDCl3): δ 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): calculated value C18H28BNO4 [M+H]+ 310.2, measured value 311.0.

References

[1] Patent: WO2006/47277, 2006, A2. Location in patent: Page/Page column 97
[2] Patent: US2006/281788, 2006, A1. Location in patent: Page/Page column 73
[3] Patent: US2008/51402, 2008, A1. Location in patent: Page/Page column 60
[4] Patent: WO2007/48088, 2007, A2. Location in patent: Page/Page column 115
[5] Patent: US2013/102601, 2013, A1. Location in patent: Paragraph 184

TERT-BUTYL 5-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-3,6-DIHYDROPYRIDINE-1(2H)-CARBOXYLATE(885693-20-9)Related Product Information

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