Cesium carbonate → N-(2-Butyl-1-benzofuran-5-yl)methanesulfonamide

Participants

Role	Name	HCID	Charge
Reactant	Cesium carbonate	HCID 10796	—
Reactant	Methanesulfonamide	HCID 72879	—
Reactant	Di-tert-butyl(2',4',6'-tris(propan-2-yl)-(1,1'-biphenyl)-2-yl)phosphane	HCID 11618717	—
Reactant	5-Bromo-2-butylbenzofuran	HCID 56926023	—
Catalyst	(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladium	HCID 6505921	—
Solvent	1,4-Dioxane	HCID 31275	—
Product	N-(2-Butyl-1-benzofuran-5-yl)methanesulfonamide	HCID 9878493	—

Reaction Conditions

Temperature	100 °C

Reaction Steps

The following are placed in an equipped reactor under an argon atmosphere: 13 g of cesium carbonate (39.9 mmol), 3 g of methanesulfonamide (31.5 mmol), 250 mg of Pd(dba)2 (0.4 mmol) and 440 mg of 2-(di-tert-butylphosphino)-2′,4′,6′-triisopropyl-1,1′-biphenyl (ligand L1) (1.04 mmol). 5.5 g of 2-n-butyl-5-bromobenzofuran (compound IX or II) (21.7 mmol) dissolved in 55 ml of dioxane are then added by syringe. The reaction medium is then stirred and heated at 100° C. for 24 hours.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09334254B2
Source dataset	uspto-grants-2016_05
ORD ID	ord-42e33efc87c94afe992f645d5d6a2124
Source note	uspto-grants-2016_05