1,4-Dioxane → 5-(4-tert-butylthiazol-2-ylamino)-N-(2,4-dimethoxybenzyl)-N-(thiazol-2-yl)pyridine-2-sulfonamide

Participants

Role	Name	HCID	Charge
Reactant	1,4-Dioxane	HCID 31275	—
Reactant	2-Amino-4-(4-chlorophenyl)thiazole	HCID 73241	—
Reactant	1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)	HCID 636044	—
Reactant	Sodium t-butoxide	HCID 23676156	—
Reactant	N-(2,4-dimethoxybenzyl)-5-iodo-N-(thiazol-2-yl)pyridine-2-sulfonamide	HCID 57551263	—
Catalyst	Bis(dibenzylideneacetone)palladium	HCID 9811564	—
Product	5-(4-tert-butylthiazol-2-ylamino)-N-(2,4-dimethoxybenzyl)-N-(thiazol-2-yl)pyridine-2-sulfonamide	HCID 57551262	—

Reaction Conditions

Temperature	150 °C

Reaction Steps

Into a Vial was added the 5-Iodo-pyridine-2-sulfonic acid (2,4-dimethoxy-benzyl)-thiazol-2-yl-amide (80 mg, 0.0001 mol), Sodium tert-butoxide (43 mg, 0.00044 mol), 9,9-DIMETHYL-4,5-BIS(DIPHENYLPHOSPHINO)XANTHENE (1.0E1 mg, 0.000018 mol), Tris(dibenzylideneacetone)dipalladium(0) (5.4 mg, 0.0000059 mol), 2-AMINO-4-(4-CHLOROPHENYL)THIAZOLE and the de-gassed anhydrous 1,4-Dioxane (2.0 mL, 0.026 mol). The reaction mixture was heated at 150° C. for 1 h in microwave. The reaction mixture was filtered through Celite and the filtrate was concentrated to give the crude product that was purified on ISCO twice (10% to 100% E/H) to give the product as a light brown solid.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08124610B2
Source dataset	uspto-grants-2012_02
ORD ID	ord-94b6ffa27ce34f719937bb102bc66de9
Source note	uspto-grants-2012_02