2-(Dimethylamino)ethanol → (E)-N-(3-(2-ethoxyvinyl)-4-(N-(1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-6-yl)sulfamoyl)phenyl)-2,2,2-trifluoroacetamide

Participants

Role	Name	HCID	Charge
Reactant	2-(Dimethylamino)ethanol	HCID 7902	—
Reactant	Stannane, tributyl(2-ethoxyethenyl)-	HCID 6508882	—
Reactant	N-(3-bromo-4-(N-(1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-6-yl)sulfamoyl)phenyl)-2,2,2-trifluoroacetamide	HCID 86655204	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	N-methyl-2-pyrrolidone	HCID 13387	—
Product	(E)-N-(3-(2-ethoxyvinyl)-4-(N-(1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-6-yl)sulfamoyl)phenyl)-2,2,2-trifluoroacetamide	HCID 86655212	—

Reaction Conditions

Temperature	100 °C

Reaction Steps

The mix of N-(3-bromo-4-(N-(1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-6-yl)sulfamoyl)phenyl)-2,2,2-trifluoroacetamide (87 mg, 0.182 mmol), (E)-tributyl(2-ethoxyvinyl) stannane (71 mg, 0.196 mmol), dimethylamino ethanol (17.9 mg, 0.2 mmol) and Pd(dppf)2Cl2 in NMP (2 ml) was degassed and heated to 100° C. overnight. The crude product was purified by prep-HPLC to give (E)-N-(3-(2-ethoxyvinyl)-4-(N-(1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-6-yl)sulfamoyl)phenyl)-2,2,2-trifluoroacetamide.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08461134B2
Source dataset	uspto-grants-2013_06
ORD ID	ord-e9b0dc2119444dc39faf782e8ca09162
Source note	uspto-grants-2013_06