Sodium Bicarbonate → HCID 86713199, compound

Participants

Role	Name	HCID	Charge
Reactant	Sodium Bicarbonate	HCID 516892	—
Reactant	2,2-difluoro-1-((4S,5R)-4-(fluoromethyl)-2,2-dimethyl-5-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)oxazolidin-3-yl)ethanone	HCID 86695414	—
Reactant	HCID 86713198	HCID 86713198	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	Toluene	HCID 1140	—
Solvent	Isopropanol	HCID 3776	—
Product	HCID 86713199	HCID 86713199	34.5%

Reaction Conditions

Temperature	75 °C

Reaction Steps

A solution of the product of step 2, Example 28 (1 g, 3 mmol) and the product of step 4, Example 8 (1.26 g, 3 mmol) in toluene 20 ml and isopropyl alcohol (20 mL) is treated with sodium hydrogen carbonate saturate solution (10 ml). The mixture is deoxygenated and PdCl2(dppf) (111 mg, 0.15 mmol) is added and the reaction mixture deoxygenated again. The mixture is heated at 75° C. overnight. The reaction mixture is partitioned between ethyl acetate (100 ml) and water (50 ml). The phases were separated, the aqueous extracted with ethylacetate and the combined organic layers evaporated. Column chromatography (0-50% ethyl acetate in heptane) gave the title compound (554 mg). MS (ESI+) m/z 536.0 [M+H].

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09206126B2
Source dataset	uspto-grants-2015_12
ORD ID	ord-96e72c683df64d699e14bdb9b362e0c7
Source note	uspto-grants-2015_12