Sodium Carbonate → HCID 178421998, compound

Participants

Role	Name	HCID	Charge
Reactant	Sodium Carbonate	HCID 10340	—
Reactant	Triphenylphosphine	HCID 11776	—
Reactant	5-Methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,4-dihydro-2H-1-benzopyran	HCID 57416223	—
Reactant	4-Bromo-3-(2-tert-butylsilyloxypropan-2-yl)-7-phenylmethoxyisochromen-1-one	HCID 131732825	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	1,4-Dioxane--water (1/1)	HCID 21886435	—
Product	HCID 178421998	HCID 178421998	14.6%

Reaction Steps

To a solution of 7-Benzyloxy-4-bromo-3-(tert-butyl-dimethyl-silanyloxymethyl)-isochromen-1-one (30 g, 63.1 mmol) and 4,4,5,5-tetramethyl-2-(5-methylchroman-6-yl)-1,3,2-dioxaborolane (51.9 g, 89 mmol) in 1,4-dioxane/H2O (400/100 mL) was added Pd(dppf)Cl2 (4.62 g, 6.31 mmol), Na2CO3 (20 g, 189 mmol), and PPh3 (4.96 g, 18.93 mmol). The resultant mixture was stirred at refluxing under N2. After 12 h, the reaction mixture was cooled to ambient temperature and partitioned between dichloromethane and water. The organic layer was washed with brine, dried (MgSO4), filtered and concentrated in vacuo. The residue was purified by chromatography column on silica gel to afford title product as a pale solid (5.0 g). LCMS (10-80 AB—2MIN.M): Rt=1.541, purity=93.3%, M+1=542.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09029391B2
Source dataset	uspto-grants-2015_05
ORD ID	ord-795f411b8cb642719488469ff3634dfa
Source note	uspto-grants-2015_05