2,6-Dimethylaniline → HCID 12545262, compound

Participants

Reaction Conditions

Reaction Steps

A solution of ligand 1 (see FIG. 1) [42 mg, 0.1 mmol (8.4 mg, 0.02 mmol, 4 mol % per reaction)] and NaOt-Bu [10 mg, 0.1 mmol (2 mg, 0.02 mmol, 4 mol % per reaction)] were stirred in 5 mL DME (anhy). After 10 minutes, 1 mL of the solution was added via syringe to a test tube containing (under an Argon atmosphere) Pd2(dba)3 (4.6 mg, 0.005 mmol, 2 mol % Pd), K3PO4 (148 mg, 0.7 mmol), 2-chloronitrobenzene (79 mg, 0.5 mmol), and 2,6-dimethylaniline (74 μL, 0.6 mmol). The test tube was capped (with a proper cap-no rubber septa) and heated at 100° C. for 18 hours. The reaction mixture was allowed to cool to r.t., diluted with ether and dodecane was added as an internal standard. The reaction mixture was purified by column chromatography (5% EtOAc/hexanes) to yield 110 mg (91% yield) of the product.

Provenance & Evidence