2-Pyridinemethanamine → HCID 24954097, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of pyridin-2-ylmethanamine (0.105 g, 1.0 mmol) and (R)—N-(3-bromo-4-chlorobenzyl)-1-phenylethanamine 73 (0.251 g, 0.8 mmol) was added sodium 2-methylpropan-2-olate (0.103 g, 1 mmol), Pd2(dba)3 (0.051 g, 0.06 mmol), 2-(diphenylphosphino)-1-(2-(diphenylphosphino)naphthalen-1-yl)naphthalene (0.210 mg, 0.34 mmol), and toluene (1.5 mL). The reaction mixture was degassed by bubbling nitrogen through the solution for 15 min and heated to 80° C. After 20 h, the reaction mixture was diluted with EtOAc and saturated NaHCO3. The organic phase was washed with brine (1×), dried over MgSO4, filtered, and concentrated in vacuo. Purification by flash column chromatography on silica gel (eluted with 60% to 100% EtOAc in hexanes) followed by flash column chromatography on silica gel (eluted with 1% to 5% MeOH (2 M in NH3) in DCM) gave (R)-2-chloro-5-((1-phenylethylamino)methyl)-N-(pyridin-2-ylmethyl)benzenamine 74 (0.034 g, 12% yield) as a colorless oil. 1H NMR (400 MHz, CDCl3) δ 1.31 (d, J=6.5 Hz, 3H), 3.46 (d, J=13.3 Hz, 1H), 3.55 (d, J=13.3 Hz, 1H), 3.72 (q, J=6.5 Hz, 1H), 4.53 (d, J=5.5 Hz, 2H), 5.38 (m, 1H), 6.54-6.58 (m, 2H), 7.20-7.33 (m, 9H), 7.66 (td, J=7.6, 1.8 Hz, 1H), 8.62 (d, J=4.3 Hz, 1H). Mass spectrum: calculated for C21H22ClN3 351.2. found 352.2 (M++1).

Provenance & Evidence