Potassium Phosphate, Tribasic → 5-(3,3,6-Trimethyl-2,3-dihydrobenzo[3,4-b]furan-5-yl)-2-pyridylamine

Participants

Role	Name	HCID	Charge
Reactant	Potassium Phosphate, Tribasic	HCID 62657	—
Reactant	5-Bromo-3,3,6-trimethyl-2,3-dihydro-benzofuran	HCID 18699201	—
Reactant	N-(5-(2,2-difluoro-6-methylbenzo[d][1,3]dioxol-5-yl)pyrazin-2-yl)-2-fluorobenzamide	HCID 58486754	—
Solvent	Water	HCID 962	—
Solvent	Acetonitrile	HCID 6342	—
Solvent	1,4-Dioxane	HCID 31275	—
Product	5-(3,3,6-Trimethyl-2,3-dihydrobenzo[3,4-b]furan-5-yl)-2-pyridylamine	HCID 58487135	90.8%

Reaction Conditions

Temperature	85 °C

Reaction Steps

A mixture of 5-bromo-3,3,6-trimethyl-2,3-dihydrobenzo[b]furan (171) (241 mg, 1 mmol), 2-aminopyridine-5-boronic acid pinacol ester (11) (330 mg, 1.5 mmol), bis(ditertbutyl(4-dimethylaminophenyl)phosphine)dichloropalladium (II) (106 mg), and K3PO4 (636 mg) in 3 ml ACN, 3 ml dioxane, 1.5 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 silica gel column purification to give 231 mg 5-(3,3,6-trimethyl-2,3-dihydrobenzo[3,4-b]furan-5-yl)-2-pyridylamine (172) (yield: 90.8%, purity>95%) as thick yellow oil.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09120751B2
Source dataset	uspto-grants-2015_09
ORD ID	ord-d6c377934fc54b86866510ec79ebc4a1
Source note	uspto-grants-2015_09