Dimethylformamide → tert-Butyl 4-(2-(benzo[d]thiazol-2-ylethynyl)-8-morpholinoimidazo[1,2-a]pyrazin-5-yl)benzoate

Participants

Role	Name	HCID	Charge
Reactant	Dimethylformamide	HCID 6228	—
Reactant	2-Bromothiazole	HCID 76430	—
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	tert-Butyl 4-(2-ethynyl-8-morpholinoimidazo[1,2-a]pyrazin-5-yl)benzoate	HCID 117732303	—
Catalyst	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 44119782	—
Product	tert-Butyl 4-(2-(benzo[d]thiazol-2-ylethynyl)-8-morpholinoimidazo[1,2-a]pyrazin-5-yl)benzoate	HCID 117732304	—

Reaction Steps

Compound 81b (95.0 mg, 0.23 0 mmol) and 2-bromothiazole (430 mg, 2.00 mmol) were placed in a vial and purged with Argon. Anhydrous DMF (2 mL) and DIEA (0.410 mL, 2.35 mmol) were added. The mixture was degassed and purged with Argon. CuI (2.24 mg, 0.0120 mmol) and dichloro(1,1′-bis(diphenylphosphino)ferrocene)palladium(II) dichloromethane adduct (16.5 mg, 0.0230 mmol) were added. The reaction was stirred at rt for 4 h. The reaction was filtered through a pad of diatomaceous earth and the filter cake was rinsed with EtOAc. The combined filtrates were washed with brine and water, dried, and concentrated. The residue was purified with preparative TLC (EtOAc/dichloromethane; 3:7) to obtain compound 81c. Mass Spectrum (LCMS, ESI pos.): Calcd. for C30H28N5O3S: 538.2 (M+H). found: 538.5.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09249163B2
Source dataset	uspto-grants-2016_02
ORD ID	ord-5028abe7dca7455ebae43cc20c12019c
Source note	uspto-grants-2016_02