2-Bromo-5-methylpyridine → HCID 58333407, compound

https://huagongshe.com/reaction/2066890

Participants

Role	Name	HCID	Charge
Reactant	2-Bromo-5-methylpyridine	HCID 564216	—
Reactant	1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)	HCID 636044	—
Reactant	Sodium t-butoxide	HCID 23676156	—
Reactant	1-(2-Fluoro-4-methanesulfonyl-phenyl)-piperidin-4-one O-piperidin-4-yl-oxime	HCID 86655022	—
Catalyst	Bis(dibenzylideneacetone)palladium	HCID 9811564	—
Solvent	Toluene	HCID 1140	—
Product	HCID 58333407	HCID 58333407	—

Reaction Conditions

Temperature	100 °C

Reaction Steps

Pd2 dba3 (1.5 mg, 0.0016 mmol), Xantphos (2.8 mg, 0.0048 mmol), NaOtBu (11.5 mg, 0.12 mmol), 63a (29.5 mg, 0.08 mmol) and 2-bromo-5-methyl-pyridine (27.5 mg, 0.16 mmol) were combined. Toluene (0.3 mL) was added and the mixture was flushed with nitrogen, sealed and heated at 100° C. overnight. The solvent was removed and the crude mixture was purified on preparative HPLC to give 67-1: LC-MS 461.2 (MH+).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08293729B2
Source dataset	uspto-grants-2012_10
ORD ID	ord-13654952b0aa478d93c5f3f733dc183a
Source note	uspto-grants-2012_10