3-Chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-pyridinamine

To a solution of 5-bromo-3-chloro-pyridin-2-ylamine (2.0 g, 9.64 mmol) in 1, 4-dioxane (20 mL) were added 4, 4, 4', 4', 5, 5, 5', 5'-octamethyl-2, 2'-bi(l, 3, 2-dioxaborolane) (2.94 g, 11.57 mmol), potassium acetate (2.84 g, 28.92 mmol) and l, l'-bis(diphenylphosphino)ferrocene-palladium(n)dichloride (705 mg, 0.96 mmol). The reaction mixture was purged with nitrogen for 2 min and heated to 100 °C for 4 h and subsequently concentrated to dryness in vacuo. The resulting viscous mass was diluted with water and extracted with ethyl acetate (2 x 50 mL). The combined organic layers were dried over sodium sulfate and concentrated to dryness in vacuo. The resulting residue was purified by column chromatography (silica gel, 100-200 mesh, 30percent ethyl acetate in hexane) affording 3-chloro-5-(4, 4, 5, 5-tetramethyl-l, 3, 2-dioxaborolan-2-yl)pyridin-2-amine (2.0 g, 84percent): NMR (400 MHz, Chloroform-d) δ 8.32 (d, J = 1.6 Hz, 1H), 7.84 (d, J = 1.6 Hz, 1H), 5.09 (s, 2H), 1.32 (s, 12H).Preparative Example 10 Step 1: 3-chloro-5-(4, 4, 5, 5-tetramethyl-l, 3, 2-dioxaborolan-2-yl)pyridin-2-amine To a solution of 5-bromo-3-chloro-pyridin-2-ylamine (2.0 g, 9.64 mmol) in 1, 4-dioxane (20 mL) were added 4, 4, 4', 4', 5, 5, 5', 5'-octamethyl-2, 2'-bi(l, 3, 2-dioxaborolane) (2.94 g, 11.57 mmol), potassium acetate (2.84 g, 28.92 mmol) and 1 , l'-bis(diphenylphosphino)ferrocene-palladium(II)dichloride (705 mg, 0.96 mmol). The reaction mixture was purged with nitrogen for 2 min and heated to 100 °C for 4 h and subsequently concentrated to dryness in vacuo. The resulting viscous mass was diluted with water and extracted with ethyl acetate (2 x 50 mL). The combined organic layers were dried over sodium sulfate and concentrated to dryness in vacuo. The resulting residue was purified by column chromatography (silica gel, 100-200 mesh, 30percent ethyl acetate in hexane) affording 3-chloro-5- (4, 4, 5, 5-tetramethyl-l, 3, 2-dioxaborolan-2-yl)pyridin-2-amine (2.0 g, 84percent): H NMR (400 MHz, Chloroform-d) δ 8.32 (d, J = 1.6 Hz, 1H), 7.84 (d, J = 1.6 Hz, 1H), 5.09 (s, 2H), 1.32 (s, 12H).9.2 Boronate 13: Compound 12 (4 g, 17.2 mmol), bis (pinacolato) diboron (4.79 g, 18.8 mmol), KOAc (3.37 g, 34.2 mmol) and Pd (dppf) Cl9.2 Boronate 13: Compound 12 (4 g, 17.2 mmol), bis(pinacolato)diboron (4.79 g, 18.8 mmol), KOAc (3.37 g, 34.2 mmol) and Pd(dppf)Cl

Molecular Weight:254.52
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:1
Exact Mass:254.0993356
Monoisotopic Mass:254.0993356
Topological Polar Surface Area:57.4
Heavy Atom Count:17
Complexity:285
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes