Ethanethiol → 5-Ethylsulfanyl-1,3-dihydro-isoindole-2-carboxylic acid tert-butyl ester

Participants

Role	Name	HCID	Charge
Reactant	Ethanethiol	HCID 6343	—
Reactant	N-Boc-5-bromoisoindoline	HCID 16102683	—
Reactant	Sodium t-butoxide	HCID 23676156	—
Catalyst	palladium(II) acetate	HCID 167845	—
Catalyst	Bis(cyclopenta-2,4-dien-1-yl-di(propan-2-yl)phosphane);iron(2+)	HCID 15420033	—
Solvent	1,4-Dioxane	HCID 31275	—
Solvent	Tetrahydrofuran ethyl acetate	HCID 21939870	—
Product	5-Ethylsulfanyl-1,3-dihydro-isoindole-2-carboxylic acid tert-butyl ester	HCID 57753600	—

Reaction Conditions

Temperature	100 °C

Reaction Steps

Lit. Tetrahedron 2004, 60, 7397-7403. To a stirred suspension of 1.34 mmol 5-bromo-1,3-dihydro-isoindole-2-carboxylic acid tert-butyl ester (CAS: 201940-08-1) in 2 ml dioxane were added 0.03 mmol 1,1′-bis(diisopropylphosphino)ferrocene, 0.03 mmol palladium acetate, 1.61 mmol sodium tert-butoxide and 2.68 mmol ethanethiol and the mixture was stirred at 100° C. for 16 h. The reaction mixture was then cooled to room temperature, diluted with ethyl acetate/tetrahydrofuran and washed with brine. The organic phase was dried over sodium sulfate and concentrated in vacuo to yield the title compound as a brown oil which was used in the next step without further purification.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07557114B2
Source dataset	uspto-grants-2009_07
ORD ID	ord-886c094d1a944348a9fb9b3a79760189
Source note	uspto-grants-2009_07