Methyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate → HCID 10272130, compound

https://huagongshe.com/reaction/432085

Participants

Role	Name	HCID	Charge
Reactant	Methyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate	HCID 2773500	—
Reactant	tert-butyl [(2R)-6-iodo-3,4-dihydro-2H-chromen-2-yl]methylcarbamate	HCID 10221906	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	Toluene	HCID 1140	—
Solvent	1,4-Dioxane	HCID 31275	—
Product	HCID 10272130	HCID 10272130	83.1%

Reaction Conditions

Temperature	85 °C

Reaction Steps

A solution of methyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate (Example 15, 1.67 g, 6.36 mmol) in 130 mL toluene and 27 mL 1,4-dioxane was degassed with argon for 10 minutes. tert-Butyl [(2R)-6-iodo-3,4-dihydro-2H-chromen-2-yl]methylcarbamate (Example 12, 1.65 g) and 265 mg (3 mol %) Pd(dppf)Cl2 were then added, and the solution was degassed with argon for an additional 5 minutes. Finally, 26.5 mL of 2M aqueous sodium carbonate was added and the solution was stirred at 85° C. for 16 hours. This mixture was then cooled to ambient temperature, filtered through a pad of Celite®, and concentrated in vacuo. The product was then purified by Biotage (100% methylene chloride to 3% MeOH: methylene chloride) to obtain 1.40 g of product. m/z=397.9 [M+].

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US06660752B2
Source dataset	uspto-grants-2003_12
ORD ID	ord-9d8838465fa346c18a12405a453ab4d5
Source note	uspto-grants-2003_12