4-(5-Fluoro-4-iodo-2-methylphenyl)-2-methylpyridine → Tert-butyl 2-(2-fluoro-5-methyl-4-(2-methylpyridin-4-yl)phenyl)acetate

Participants

Role	Name	HCID	Charge
Reactant	4-(5-Fluoro-4-iodo-2-methylphenyl)-2-methylpyridine	HCID 58447915	—
Reactant	HCID 178451183	HCID 178451183	—
Catalyst	Bis(dibenzylideneacetone)palladium	HCID 9811564	—
Catalyst	Ditert-butyl(cyclopenta-2,4-dien-1-yl)phosphane;iron(2+);(2,3,4,5-tetraphenylcyclopenta-1,4-dien-1-yl)benzene	HCID 129828017	—
Solvent	Tetrahydrofuran	HCID 8028	—
Product	Tert-butyl 2-(2-fluoro-5-methyl-4-(2-methylpyridin-4-yl)phenyl)acetate	HCID 58447700	—

Reaction Conditions

Temperature	70 °C

Reaction Steps

To a seal tube charged with 4-(5-fluoro-4-iodo-2-methylphenyl)-2-methylpyridine 191-4 (200 mg, 0.6 mmol), Pd2(dba)3 (28 mg, 0.03 mmol), and Q-Phos (21 mg, 0.03 mmol) was added anhydrous THF (2.5 mL). The reaction vessel was flushed with nitrogen and (2-tert-butoxy-2-oxoethyl)zinc(II) chloride (0.5 M in ether, 1.34 mL, 0.67 mmol) was added subsequently. The reaction was heated to 70° C. for 12 hours. The solvent was removed by rotary evaporation and the residue was purified by silica gel flash chromatography, eluted with 50% ethyl acetate in hexane to give tert-butyl 2-(2-fluoro-5-methyl-4-(2-methylpyridin-4-yl)phenyl)acetate 191-5. MS m/z 316.10 (M+1).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09238646B2
Source dataset	uspto-grants-2016_01
ORD ID	ord-c96f0cf851b04cb6bf604ca0c5eaabb0
Source note	uspto-grants-2016_01