Potassium Phosphate, Tribasic → 4-(2-Fluoro-4-trimethylsilanyl-phenylamino)-benzo[d]isothiazole-5-carboxylic acid tert-butyl ester

Participants

Role	Name	HCID	Charge
Reactant	Potassium Phosphate, Tribasic	HCID 62657	—
Reactant	1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)	HCID 636044	—
Reactant	Tert-butyl 4-bromobenzo[d]isothiazole-5-carboxylate	HCID 58374343	—
Reactant	2-Fluoro-4-(trimethylsilyl)aniline	HCID 59596599	—
Catalyst	Bis(dibenzylideneacetone)palladium	HCID 9811564	—
Solvent	Toluene	HCID 1140	—
Solvent	Ethyl Acetate	HCID 8857	—
Product	4-(2-Fluoro-4-trimethylsilanyl-phenylamino)-benzo[d]isothiazole-5-carboxylic acid tert-butyl ester	HCID 67083578	78.1%

Reaction Conditions

Temperature	90 °C

Reaction Steps

A solution of 2-fluoro-4-trimethylsilanyl-phenylamine (340 mg, 1.43 mmol), 4-bromo-benzo[d]isothiazole-5-carboxylic acid tert-butyl ester (449 mg, 1.43 mmol), Pd2 dba3 (65 mg, 0.07 mmol), Xantphos (83 mg, 0.14 mmol) and potassium phosphate tribasic (455 mg, 2.14 mmol) in toluene (5 mL) was degassed and then the reaction mixture heated at 90° C. for 18 hours. The cooled reaction mixture was diluted with ethyl acetate, filtered through Celite®, and the filtrate concentrated in vacuo. The resultant residue was subjected to flash chromatography (Si—PPC, gradient 2.5 to 5% diethyl ether in pentane) to give the title compound as a dark oil (465 mg, 78%). LCMS (Method B): RT=5.76 min, [M+H]+=417.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08841462B2
Source dataset	uspto-grants-2014_09
ORD ID	ord-08870ac8b2754831847f6c1f3cdc3533
Source note	uspto-grants-2014_09