2-Iodo-6-methylpyridine

Preparation 9 The title compound was prepared following the procedure reported above for the compound of replacing Compound llOa for Compound la and 2-iodo-6-methylpyridine for 3-chlorobenzoyl chloride. After the usual work-up, the reaction crude was purified by automated flash chromatography (SP1® Biotage, 10 g SNAP column) eluting with PE - EtOAc gradient from 9:1 to 6:4 affording the title product as a dense colourless oil (77.8 percent). E/Z mixture 55:45 (1H-NMR).UPLC-MS [M+H]= 353.16, 353.231H NMR (400 MHz, CHLOROFORM-d) mix of isomers oe ppm 7.57 (br s, 2 H), 7.20 - 7.27 (m, 2 H), 7.10 (br d, 2 H), 5.69 (s, 1 H) and 5.62 (s, 1 H), 3.26 - 3.41 (m, 4 H), 2.82 (s, 2 H), 2.59 (br s, 6 H), 2.51 (s, 2 H) and 2.53 (br s, 2 H), 2.23 - 2.34 (m, 4 H), 2.21 (m, 2 H) and 1.94 - 2.12 (m, 4 H), 1.62 - 1.81 (m, 4 H), 1.49 (m, 18 H)A mixture of Compound la (55 mg, 0.171 mmol) 2-bromo-6-methylpyridine (23.4 ul, 0.205 mmol), tetrakis(triphenylphosphine)palladium (7.89 mg, 0.007 mmol), sodium acetate (28 mg, 0.342 mmol) and tetrabutylammonium fluoride (44.7 mg, 0.17 1 mmol)) in anhydrous DMF (3 mL) was heated at 110°C into a microwave oven (Biotage Smith Creator®) for 10 mm then cooled at r.t.. The reaction mixture was poured into water and extracted with EtOAc (3x). The organic layer was dried over Na2504 and the solvent was evaporated to dryness to give a crude which was purified via automated flashchromatography (SP1® Biotage, SNAP25 Cartridge), eluting with a EtOAc - PetroleumEther gradient from 75:25 to 1:1 to give mg 51(87.6percent) of the title compound.UPLC-MS [M+H]= 341.521H NMR (400 MHz, DMSO-d6) oe ppm 7.68 (t, 1 H), 7.31 (d, 1 H), 7.22 (d, 1 H), 5.66 (s, 1 H), 3.43 (brt, 2 H), 3.15 (s, 2 H), 2.62 (brt, 2 H), 2.45 (s, 3 H), 1.42 (s, 9 H), 1.08 (s, 6H)

Molecular Weight:219.02
XLogP3:2
Hydrogen Bond Acceptor Count:1
Exact Mass:218.95450
Monoisotopic Mass:218.95450
Topological Polar Surface Area:12.9
Heavy Atom Count:8
Complexity:74.9
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes