Hydrochloric Acid → HCID 66742859, compound

Participants

Reaction Steps

To a round bottomed flask charged with 2-chloro-5-((3-methoxyazetidin-1-yl)methyl)pyridine (11.5 g, 54.1 mmol, Eq: 1.00), tris(dibenzylideneacetone)dipalladium(0) (1.24 g, 1.35 mmol, Eq: 0.025), and biphenyl-2-yldicyclohexylphosphine (948 mg, 2.7 mmol, Eq: 0.05) was added toluene (150 ml) followed immediately by lithium bis(trimethylsilyl)amide (81.1 ml, 81.1 mmol, Eq: 1.5) as a 1.0 M solution in THF. Brought quickly to reflux and stirred overnight under Argon. Next day, the reaction was checked by TLC (9:1 MC:MeOH) and the starting material was gone, replaced primarily by a single lower Rf spot. Cooled while stirring and added 5 ml of 1.0M HCl. Stirred 20 min and filtered over celite. The filtrate was diluted with ether and washed with 200 mL of 1.0M NaOH followed by water and brine. Dried the org phase over sodium sulfate, filtered and removed solvent. Obtained a dark red oil weighing 14.4 g. Took the oil up in CH2Cl2 and flashed (neat MC to 90:10 MC:MeOH:0.1 Et3N). Collected 4.4 g (42.1%) of cleanest fractions as a reddish oil for next step.

Provenance & Evidence