Boronic acid, B-(2-(((1,1-dimethylethyl)amino)sulfonyl)phenyl)- → HCID 68312991, compound

Participants

Role	Name	HCID	Charge
Reactant	Boronic acid, B-(2-(((1,1-dimethylethyl)amino)sulfonyl)phenyl)-	HCID 4997616	—
Reactant	8-bromo-2-(2-isopropyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-1,3a-diaza-benzo[e]azulene	HCID 58204313	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	1,4-Dioxane	HCID 31275	—
Product	HCID 68312991	HCID 68312991	93.1%

Reaction Conditions

Temperature	100 °C

Reaction Steps

A mixture of 12-bromo-4-[1-(propan-2-yl)-1H-1,2,4-triazol-5-yl]-9-oxa-3,6-diazatricyclo[8.4.0.02,6]tetradeca-1(14),2,4,10,12-pentaene (200 mg, 0.53 mmol), 2-(N-tert-butylsulfamoyl)phenylboronic acid (274 mg, 1.07 mmol), Pd(dppf)Cl2 (38.9 mg, 0.0530 mmol), and CS2CO3 (350 mg, 1.07 mmol) in 1,4-dioxane (5 mL) was heated to 100° C. for 8 h. After filtration, the filtrate was purified by reverse phase combiflash eluting with a 0-70% gradient of CH3CN in 0.3% NH4HCO3 to afford N-tert-butyl-2-{4-[1-(propan-2-yl)-1H-1,2,4-triazol-5-yl]-9-oxa-3,6-diazatricyclo[8.4.0.02,6]tetradeca1(14),2,4,10,12-pentaen-12-yl}benzene-1-sulphonamide (250 mg, 93% yield) as white solid. LCMS (ESI) m/z: 507.2 [M+H+]

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09090628B2
Source dataset	uspto-grants-2015_07
ORD ID	ord-51125eab1a2e4d2b809003612a1fc560
Source note	uspto-grants-2015_07