Ethyl Acetate → 5-(3,5-Dimethylbenzo[d]isoxazol-6-yl)-2-pyridylamine

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)pyridin-2-amine	HCID 2756555	—
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-Dimethylbenzo[d]isoxazol-6-yl)-2-pyridylamine	HCID 58486967	91.9%

Reaction Conditions

Temperature	85 °C

Reaction Steps

A mixture of 6-bromo-3,5-dimethylbenz[d]isoxazole (104) (46 mg, 0.2 mmol), 2-aminopyridine-5-boronic acid pinacol ester (11) (66 mg, 0.3 mmol), bis(ditertbutyl(4-dimethylaminophenyl)phosphine)dichloropalladium (II) (21 mg, 10% mol) and K3PO4 (64 mg, 0.3 mmol) in 0.5 ml ACN, 0.5 ml dioxane, 0.25 ml H2O was bubbled with argon before heated at 85° C. for 2.5 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-dimethylbenzo[d]isoxazol-6-yl)-2-pyridylamine (105) (44 mg, yield: 91.9%, purity>90%) as yellow solid.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08980629B2
Source dataset	uspto-grants-2015_03
ORD ID	ord-a58b3515a08d45b88a2f0249172f12eb
Source note	uspto-grants-2015_03