Diisopropylamine → (S)-2'-amino-3-(3,3-dimethylbut-1-ynyl)-5'H-spiro[chromeno[2,3-b]pyridine-5,4'-oxazol]-7-ol

Participants

Role	Name	HCID	Charge
Reactant	Diisopropylamine	HCID 7912	—
Reactant	3,3-Dimethyl-1-butyne	HCID 13512	—
Reactant	(S)-2'-amino-3-bromo-5'H-spiro[chromeno[2,3-b]pyridine-5,4'-oxazol]-7-ol	HCID 58466114	—
Catalyst	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
Catalyst	HCID 178418397	HCID 178418397	—
Solvent	Tetrahydrofuran	HCID 8028	—
Product	(S)-2'-amino-3-(3,3-dimethylbut-1-ynyl)-5'H-spiro[chromeno[2,3-b]pyridine-5,4'-oxazol]-7-ol	HCID 67248031	—

Reaction Conditions

Temperature	80 °C

Reaction Steps

A vial charged with (S)-2′-amino-3-bromo-5′H-spiro[chromeno[2,3-b]pyridine-5,4′-oxazol]-7-ol (0.250 g, 0.718 mmol), Pd(PPh3)4 (0.083 g, 0.072 mmol), and copper(i) iodide (0.014 g, 0.072 mmol), was treated with 1 mL THF followed by diisopropylamine (1.535 mL, 10.77 mmol). The solution was degassed with argon and 3,3-dimethylbut-1-yne (0.295 g, 3.59 mmol) was added and the vial heated to 80° C. overnight. The reaction mixture was purified directly by column chromatography yielding (S)-2′-amino-3-(3,3-dimethylbut-1-ynyl)-5′H-spiro[chromeno[2,3-b]pyridine-5,4′-oxazol]-7-ol.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08883782B2
Source dataset	uspto-grants-2014_11
ORD ID	ord-563ee1b70bce46db8f331e0599fad520
Source note	uspto-grants-2014_11