Ethyl Acetate → 5-(3,5-Dimethylbenz[d]isoxazol-6-yl)pyrazine-2-ylamine

Participants

Role	Name	HCID	Charge
Reactant	Ethyl Acetate	HCID 8857	—
Reactant	Potassium Phosphate, Tribasic	HCID 62657	—
Reactant	5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyrazin-2-amine	HCID 17998987	—
Reactant	6-Bromo-3,5-dimethylbenzo[d]isoxazole	HCID 58487070	—
Solvent	Water	HCID 962	—
Solvent	Acetonitrile	HCID 6342	—
Solvent	1,4-Dioxane	HCID 31275	—
Product	5-(3,5-Dimethylbenz[d]isoxazol-6-yl)pyrazine-2-ylamine	HCID 58486679	26.1%

Reaction Conditions

Temperature	85 °C

Reaction Steps

A mixture of 6-bromo-3,5-dimethylbenz[d]isoxazole (104) (54 mg, 0.24 mmol), 2-aminopyrazine-5-boronic acid pinacol ester (14) (79 mg, 0.358 mmol), bis(ditertbutyl(4-dimethylaminophenyl)phosphine)dichloropalladium (II) (25 mg, 10% mol) and K3PO4 (76 mg) in 1 ml ACN, 1 ml dioxane, 0.5 ml H2O was bubbled with argon before heated at 85° C. for 3 h. After cooling down to r.t., the reaction mixture was taken up in EA, washed with aq. NaHCO3 and brine. Org. phase was dried over Na2SO4, concentrated and then subjected to silica gel flash column chromatography (0-100% B, A: hexane; B: EA) to give 5-(3,5-dimethylbenz[d]isoxazol-6-yl)pyrazine-2-ylamine (109) (15 mg, yield: 26.1%, purity>95%) as light yellow solid.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08546403B2
Source dataset	uspto-grants-2013_10
ORD ID	ord-7e5a26f73e6c4ef581a194d87584f0fc
Source note	uspto-grants-2013_10