1-benzyl-1,2,5,6-tetrahydropyridin-3-ylboronic acid pinacol ester

A solution of Intermediate 132 (300 mg, 0.82 mmol), l-benzyl-5-(4, 4, 5, 5- tetramethyl-l, 3, 2-dioxaborolan-2-yl)-l, 2, 3, 6-tetrahydropyridine (245.78 mg, 0.82 mmol) and 2M aqueous Na2C03 solution (1.23 mL) in 1, 4-dioxane (10 mL) was degassed with N2 for 10 minutes, then Pd(dppf)Cl2 (67.08 mg, 0.08 mmol) was added. The mixture was heated at 60C for 1 h, then cooled to r.t. and partitioned between EtOAc (50 mL) and water (20 mL). The aqueous layer was extracted with EtOAc (2 x 25 mL), then the combined organic layers were dried (Na2S04) and the solvent was removed in vacuo. The residue was purified by column chromatography (Si02; 0-10% MeOH/EtOAc) to give the title compound (300 mg, 80%). deltaEta (500 MHz, CDC13) 7.39 (s, 2H), 7.31 (t, J 7.4 Hz, 2H), 7.26 (s, IH, includes chloroform peak), 7.16 (d, J 8.2 Hz, IH), 6.97 (d, J 8.2 Hz, IH), 6.58 (d, J 3.9 Hz, IH), 5.11 (q, J 14.5 Hz, 2H), 4.59 (q, J 6.8 Hz, IH), 3.72 (s, 2H), 3.65 (s, 3H), 3.48 (s, 2H), 2.64 (s, 2H), 2.36 (d, J 37.3 Hz, 2H), 2.19 (s, 3H), 2.08 (s, 3H), 1.57 (d, J 12.3 Hz, 2H), 1.52 (d, J 6.8 Hz, 3H). Method B HPLC-MS: MH+ mlz 458, RT 1.38 minutes (99%)A suspension of Intermediate 137 (1.5 g, 4.07 mmol) in 1, 4-dioxane (15 mL) was treated with l-benzyl-5-(4, 4, 5, 5-tetramethyl-l, 3, 2-dioxaborolan-2-yl)-l, 2, 3, 6-tetrahydro- pyridine (1.34 g, 4.48 mmol) and 2M aqueous Na2C03 solution (6.1 mL, 12.2 mmol). The mixture was degassed with N2 for 5 minutes, then Pd(dppf)Cl2'DCM (333 mg, 0.41 mmol) was added. The mixture was heated at 60C for 3 h, then cooled and partitioned between EtOAc (50 mL) and water (50 mL). The aqueous layer was extracted with EtOAc (2 x 30 mL) and the combined organic layers were washed with brine (40 mL), then dried (MgS04). The solvent was removed in vacuo. The residue was purified by column chromatography (Si02; 0-10% MeOH/EtOAc) to afford the title compound (983 mg, 51%). deltaEta (500 MHz, CDC13) 7.46-7.27 (m, 5H), 6.74 (dd, J 11.3, 1.6 Hz, 1H), 6.62 (s, 1H), 5.96 (s, 1H), 4.96 (s, 2H), 4.67 (s, 2H), 3.69 (s, 2H), 3.64 (s, 3H), 3.21 (s, 2H), 2.60 (s, 2H), 2.32 (s, 2H), 2.15 (s, 3H), 2.12 (s, 3H). Method B HPLC-MS: MH+ mlz 461 , RT 1.52 minutes (98%)Under nitrogen protection, In the three reaction bottles to join90mLDMSO, Iodine (15.8 g), 0.39 g (0.53 mmol) of PdCl2dppf, 14.5 g (0.15 mol) of anhydrous potassium acetate, And boronic acid pinacol ester 13.4 g (53 mmol) were addedGradually slow warming to completeThe mixture was stirred at 80 C overnight. The reaction was complete by GC (product / raw material> 100: 1). After filtration, the filtrate was evaporated to dryness. Ethyl acetate and activated charcoal were added and the mixture was refluxed for 1 hour. After adding ethanol and n-heptane, the reaction was cooled to -10 C and stirred to obtain 12.4 g of

Molecular Weight:299.2
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:3
Exact Mass:299.2056592
Monoisotopic Mass:299.2056592
Topological Polar Surface Area:21.7
Heavy Atom Count:22
Complexity:411
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes