Cyclohexylamine → Cyclohexyl-(3-methyl-pyridin-2-yl)-amine

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Ref: EN07957-77 BIS(DIBENZYLIDENEACETONE)PALLADIUM(Pd2((dba)3) (0.101 g, 0.11 mmol) and 2,2'-bis(diphenylphosphanyl)-1,1'-binaphthalene (BINAP) (0.136 g, 0.22 mmol) was was stirred in toluene (16.5 mL) under N2. Then 2-bromo-3-methylpyridine (1.619 mL, 14.53 mmol), cyclohexanamine (1.662 mL, 14.53 mmol) and sodium 2-methylpropan-2-olate (2.430 g, 25.29 mmol) was added to the above reaction mixture under N2.The reaction mixture was degasssed by reapeated 3 times with N2 and vaccum before the reaction mixture was heated at 115 °C for 1.5h LCMS indicated no SM left. The reaction mixture was cooled to rt, and then diluted with EtOAc and H2O. and neutralized by citric acid to PH ca 5. The aqoeus phase was extracted with EtOAc (4 x). The combined organic layers were dried over Na2SO4 and concentrated. The residue was purified automated flash chromatography on 100 g column. A gradient from 0 % to 30 % of EtOAc in heptane over 1800 mL was used as mobile phase. The product was collected using the wavelength 249 nm. Collect: F10, 0.231 g, light yellowish solid. LCMS ok, NMR ok F11-13: 1.398 g, light yellowish solid, LCMS ok, NMR ok F14-16, 79 mg, light yellowish solid, LCMS ok, NMR ok NMR of F11-13 1H NMR (500 MHz, DMSO) d 1.09 - 1.2 (m, 1H), 1.2 - 1.37 (m, 4H), 1.61 (d, 1H), 1.71 (d, 2H), 1.90 (d, 2H), 2.01 (s, 3H), 3.86 (ddd, 1H), 5.28 (d, 1H), 6.39 (dd, 1H), 7.09 - 7.22 (m, 1H), 7.83 (dd, 1H). Expected Number of Hs: 18 Assigned Hs: 18. [M + H]\+ 191.2

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