(6'-BroMo-3,4,5,6-tetrahydro-2H-[1,2']bipyridinyl-4-yl)-carbaMic acid tert-butyl ester, 98+% C15H22BrN3O2, MW: 356.27

A mixture of 2, 6-dibromo-pyridine (3.5 g, 14.77 mmol) and piperidin-4-yl-carbamic acid te/f-butyl ester (1.478 g, 7.38 mmol) is heated to 130 Step 6: tert-butyl 1-(6-(2-(benzyloxy)-1 , 1, 3, 3-tetramethyl-2, 3-dihydro- 1H-inden-5- yl)pyridin-2-yl)piperidin-4-ylcarbamate:Nitrogen was bubbled through a solution of 2-(2-(benzyloxy)-1 , 1 , 3, 3-tetramethyl-2, 3- dihydro-1 H-inden-5-yl)-4, 4, 5, 5-tetramethyl-1 , 3, 2-dioxaborolane (0.148 g, 0.365 mmol) , tert-butyl 1 -(6-bromopyridin-2-yl)piperidin-4-ylcarbamate (0.100 g, 0.281 mmol)PdCI2(dppf) CH2CI2 (0.018 g, 0.022 mmol) and 2N aqueous sodium carbonate (0.291 mL, 0.561 mmol) in dioxane (1 .2 ml) for 10 min and subsequently heated at 90 °C for 15h. After cooling to room temperature, the reaction mixture was diluted with DCM/water and filtered through a phase separator cartridge. The filtrate was concentrated in vacuo and the residue purified by flash chromatography using a Biotage SP4 instrument to afford the title compound (0.039 g, 25percent).LCMS (Method F): RT = 2.06 min, M+H+ = 350; 1H NMR (500 MHz, CDCI3): 7.84 (d, 1 H), 7.70 (s, 1 H), 7.50 (t, 1 H), 7.40 (2, 2H), 7.38 (d, 2H), 7.30 (t, 1 H), 7.19 (d, 1 H), 7.05 (d, 1 H), 6.58 (d, 1 H), 4.80 (s, 2H), 4.49 (brs, 1 H), 4.31 (m, 2H), 3.71 (m, 2H), 3.02 (m, 2H), 2.02 (m, 2H), 1 .70 (m, 1 H), 1 .45 (s, 9H), 1 .39 (s, 3H), 1 .29 (s, 3H), 1 .27 (s, 3H).A mixture of 2, 6-dibromo-pyridine (3.5 g, 14.77 mmol) and piperidin-4-yl-carbamic acid te/f-butyl ester (1.478 g, 7.38 mmol) is heated to 130 0C in a sealed vessel for 6.5 h and 160 0C for 3 h. The residue is cooled and dissolved in CH2CI2 , washed with saturated NaHCO3 (X2), brine, dried (Na2SO4), filtered and concentrated. The residue is then separated via flash chromatography (SiO2, 10-30percent EtOAc/hexanes gradient) to give an intermediate, (6'-bromo-3, 4, 5, 6-tetrahydro-2H-[1 , 2']bipyridinyl-4-yl)-carbamic acid te/f-butyl ester (0.83 g, 32percent). MS (ESI) m/z 356.0, 358.0 (M+1 ), which is taken on to next step.

Molecular Weight:356.26
XLogP3:3.6
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:4
Exact Mass:355.08954
Monoisotopic Mass:355.08954
Topological Polar Surface Area:54.5
Heavy Atom Count:21
Complexity:351
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes