Cyclobutylamine → HCID 57691120, compound

https://huagongshe.com/reaction/219225

Participants

Role	Name	HCID	Charge
Reactant	Cyclobutylamine	HCID 75645	—
Reactant	1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)	HCID 636044	—
Reactant	Sodium t-butoxide	HCID 23676156	—
Reactant	HCID 57691075	HCID 57691075	—
Catalyst	Bis(dibenzylideneacetone)palladium	HCID 9811564	—
Solvent	Toluene	HCID 1140	—
Solvent	Dichloromethane	HCID 6344	—
Product	HCID 57691120	HCID 57691120	5.2%

Reaction Conditions

Temperature	80 °C

Reaction Steps

To a pressure vial was added sodium tert-butoxide (38 mg, 0.40 mmol), xantphos (0.12 g, 0.20 mmol), Pd2(dba)3 (61 mg, 0.066 mmol), 6-((5-bromoisoxazolo[5,4-b]pyridin-3-yl)difluoromethyl)quinoline (0.10 g, 0.27 mmol), and cyclobutanamine (0.025 mL, 0.29 mmol) in toluene (3 mL). The mixture was stirred at 80° C. for two hours then was diluted with dichloromethane and filtered through celite. Purification of the filtrate by MPLC (eluted with a gradient of 10 to 50% ethyl acetate in hexanes) afforded the product as a yellow oil (5.1 mg, 5%). MS m/z=367.0 [M+1]+ Calc'd for C20H16F2N4O: 366.4

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08198448B2
Source dataset	uspto-grants-2012_06
ORD ID	ord-a6c4d6ed57414a5781e682ebf5452713
Source note	uspto-grants-2012_06