Ethyl Acetate → 5-(5-Bromo-2,3-dihydrobenzo[3,4-b]furan-6-yl)-2-pyridylamine

Participants

Role	Name	HCID	Charge
Reactant	Ethyl Acetate	HCID 8857	—
Reactant	Potassium Phosphate, Tribasic	HCID 62657	—
Reactant	N-(5-(2,2-difluoro-6-methylbenzo[d][1,3]dioxol-5-yl)pyrazin-2-yl)-2-fluorobenzamide	HCID 58486754	—
Reactant	5,6-Dibromo-2,3-dihydrobenzofuran	HCID 58486882	—
Solvent	Water	HCID 962	—
Solvent	Acetonitrile	HCID 6342	—
Solvent	1,4-Dioxane	HCID 31275	—
Product	5-(5-Bromo-2,3-dihydrobenzo[3,4-b]furan-6-yl)-2-pyridylamine	HCID 58486970	13.9%

Reaction Conditions

Temperature	85 °C

Reaction Steps

A mixture of 5,6-dibromo-2,3-dihydrobenzo[b]furan (138) (489 mg, 1.75 mmol), 2-aminopyridine-5-boronic acid pinacol ester (11) (465 mg, 1.2 eq), bis(ditertbutyl(4-dimethylaminophenyl)phosphine)dichloropalladium (II) (124 mg, 10% mol) and K3PO4 (371 mg, 1.75 mmol) in 2 ml ACN, 2 ml dioxane, 0.5 ml H2O was bubbled with argon before heated at 85° C. for 2 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-(5-bromo-2,3-dihydrobenzo[3,4-b]furan-6-yl)-2-pyridylamine (139) (48.5 mg, yield: 9.5%) as yellow solid.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08980629B2
Source dataset	uspto-grants-2015_03
ORD ID	ord-2ab2df0877504305a3c7732b4c715f92
Source note	uspto-grants-2015_03