Diethyl Ether → HCID 131734299, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of N-(6-bromopyridazin-3-yl)pivalamide (2.00 g, 7.75 mmol), dicyclohexyl(2′,4′,6′-triisopropylbiphenyl-2-yl)phosphine (0.222 g, 0.465 mmol), and tris-dipalladium(dibenzylideneacetone) (0.213 g, 0.232 mmol) was flushed with nitrogen for 30 min. THF (20 mL) was added, followed by a 1.0 M solution of (2-tert-butoxy-2-oxoethyl)zinc(II) chloride in diethyl ether (38.7 mL, 19.4 mmol) and the reaction was sealed and stirred for 2 h at 50° C. An additional amount of (2-tert-butoxy-2-oxoethyl)zinc(II) chloride (15.5 ml, 7.75 mmol) was added and the mixture stirred for 2 h at 50 C. The resulting mixture was diluted with EtOAc and filtered, then washed with water and brine. The organic layer was dried (sodium sulfate), filtered and concentrated. MPLC (3−>30% EtOAc:Hex) provided title compound. LC-MS (IE, m/z): 294 [M+1]+.

Provenance & Evidence