4-Methoxy-alpha-toluenethiol → HCID 71076731, compound

Participants

Role	Name	HCID	Charge
Reactant	4-Methoxy-alpha-toluenethiol	HCID 80407	—
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)	HCID 636044	—
Reactant	Ethyl 4-iodo-1H-pyrazole-1-acetate	HCID 46738002	—
Catalyst	Bis(dibenzylideneacetone)palladium	HCID 9811564	—
Solvent	Ethyl Acetate	HCID 8857	—
Solvent	1,4-Dioxane	HCID 31275	—
Product	HCID 71076731	HCID 71076731	—

Reaction Conditions

Temperature	90 °C

Reaction Steps

(4-Iodo-pyrazol-1-yl)-acetic acid ethyl ester (1.8 g, 10.3 mmol), 4-methoxybenzyl mercaptan (1.43 mL, 10.3 mmol), Xantphos (0.298 g, 0.515 mmol) and then Hünig's base (3.7 mL, 21.2 mmol) were dissolved in dioxane (100 mL). The reaction was purged with N2 (g) for 10 minutes and then tris(dibenzylideneacetone)dipalladium(0) (0.235 g, 0.258 mmol) was added. The reaction was heated to 90° C. for 2 hours then cooled and diluted with EtOAc. The organic portion was washed with H2O and brine, with back-extraction, then dried and concentrated. The crude material was purified on silica gel (0-20% EtOAc in hexanes) to afford the title compound.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09260416B2
Source dataset	uspto-grants-2016_02
ORD ID	ord-5da80e79d64f4117be5f2581fb772d97
Source note	uspto-grants-2016_02