Water → Methyl 2'-fluoro-2-(2-methyl-5-oxo-1-cyclopenten-1-yl)-5'-(methyloxy)-1,1'-biphenyl-4-carboxylate

関与物質

役割	名称	HCID	仕込み量
反応物	Water	HCID 962	—
反応物	Potassium Phosphate, Tribasic	HCID 62657	—
反応物	2-Bromo-3-methyl-2-cyclopenten-1-one	HCID 4437009	—
反応物	2-Dicyclohexylphosphino-2',6'-dimethoxybiphenyl	HCID 11269872	—
反応物	Methyl 2'-fluoro-5'-(methyloxy)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,1'-biphenyl-4-carboxylate	HCID 57706776	—
触媒	palladium(II) acetate	HCID 167845	—
溶媒	Diethyl Ether	HCID 3283	—
溶媒	Tetrahydrofuran	HCID 8028	—
生成物	Methyl 2'-fluoro-2-(2-methyl-5-oxo-1-cyclopenten-1-yl)-5'-(methyloxy)-1,1'-biphenyl-4-carboxylate	HCID 57705608	78.1%

反応手順

A screw-cap vial was charged with 2-bromo-3-methyl-2-cyclopenten-1-one (available from Aldrich) (0.68 g, 3.9 mmol), 66.56A (1.00 g, 2.6 mmol), potassium phosphate (1.6 g, 7.8 mmol), 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (available from Aldrich) (0.33 g, 0.80 mmol), palladium(II) acetate (available from Aldrich) (0.058 g, 0.26 mmol), degassed THF (17 mL), and water (0.23 mL, 13 mmol). The mixture was purged three times with N2, stirred for 48 hours at room temperature under N2, filtered through silica gel (EtOAc), and concentrated. Trituration of the crude residue with ether afforded 66.56B (0.72 g, 78% yield) as a pale yellow solid.

情報源と証拠

DOI	10.6084/m9.figshare.5104873.v1
特許番号	US08030354B2
出典データセット	uspto-grants-2011_10
ORD ID	ord-ef89c3da17274987b46d8285859673b9
出典メモ	uspto-grants-2011_10