Water → 4-(2-methoxyphenoxy)-N-(4-methylthiazol-2-yl)pyridin-2-amine

Participants

Role	Name	HCID	Charge
Reactant	Water	HCID 962	—
Reactant	Potassium Phosphate, Tribasic	HCID 62657	—
Reactant	2-Amino-4-methylthiazole	HCID 74143	—
Reactant	2-Chloro-4-(2-methoxyphenoxy)pyridine	HCID 63777956	—
Catalyst	1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)	HCID 636044	—
Catalyst	Bis(dibenzylideneacetone)palladium	HCID 9811564	—
Solvent	Toluene	HCID 1140	—
Product	4-(2-methoxyphenoxy)-N-(4-methylthiazol-2-yl)pyridin-2-amine	HCID 24827109	87.3%

Reaction Steps

Using the method of Example 3, step B, 2-chloro-4-(2-methoxyphenoxy)pyridine (2.95 g, 12.5 mmol), 4-methylthiazol-2-amine (28.5 mL, 11.4 mmol), potassium phosphate (2.66 g, 12.5 mmol), Pd2(dba)3 (0.261 g, 0.285 mmol) and 4,5-bis(diphenylphosphino)-9,9-dimethyl-9H-xanthene (0.181 g, 0.313 mmol) were reacted in toluene (30 mL) and water (8 mL) to provide 4-(2-methoxyphenoxy)-N-(4-methylthiazol-2-yl)pyridin-2-amine (3.12 g, 82.2% yield) as yellow solid. 1H NMR (CDCl3) δ 8.10 (d, 1H), 7.19 (m, 1H), 7.04 (dd, 1H), 6.95 (m, 2H), 6.42 (dd, 1H), 6.24 (d, 1H), 6.14 (d, 1H), 3.71 (s, 1H), 2.12 (s, 3H); Mass spectrum (apci) m/z=314 (100) (4+H).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08022222B2
Source dataset	uspto-grants-2011_09
ORD ID	ord-c6d1495f91754a98acf2c1953d88a988
Source note	uspto-grants-2011_09