Potassium Phosphate, Tribasic → N-(4-methylthiazol-2-yl)-4-(1,2,3,4-tetrahydronaphthalen-1-yloxy)pyridin-2-amine

Participants

Role	Name	HCID	Charge
Reactant	Potassium Phosphate, Tribasic	HCID 62657	—
Reactant	2-Amino-4-methylthiazole	HCID 74143	—
Reactant	2-Chloro-4-(1,2,3,4-tetrahydronaphthalen-1-yloxy)pyridine	HCID 63778108	—
Catalyst	1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)	HCID 636044	—
Catalyst	Bis(dibenzylideneacetone)palladium	HCID 9811564	—
Product	N-(4-methylthiazol-2-yl)-4-(1,2,3,4-tetrahydronaphthalen-1-yloxy)pyridin-2-amine	HCID 24825975	68.33%

Reaction Steps

Using the method of Example 3, Step B, 4-methylthiazol-2-amine (11.59 mL, 4.637 mmol), 2-chloro-4-(1,2,3,4-tetrahydronaphthalen-1-yloxy)pyridine (1.095 g, 4.216 mmol), potassium phosphate (0.9844 g, 4.637 mmol), Pd2(dba)3 (0.09651 g, 0.1054 mmol) and 4,5-bis(diphenylphosphino)-9,9-dimethyl-9H-xanthene (0.06586 g, 0.1138 mmol) were reacted to provide N-(4-methylthiazol-2-yl)-4-(1,2,3,4-tetrahydronaphthalen-1-yloxy)pyridin-2-amine (0.972 g, 68.33% yield). 1H NMR (d6-DMSO) δ 10.96 (s, 1H), 8.14 (d, 1H), 7.27 (m, 2H), 7.19 (t, 2H), 6.68 (m, 1H), 6.66 (s, 1H), 6.50 (d, 1H), 5.56 (t, 1H), 2.84 (m, 1H), 2.74 (m, 1H), 2.23 (s, 3H), 2.03 (m, 2H), 1.81 (m, 2H); Mass spectrum (apci) m/z=338.0 (M+H).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08022222B2
Source dataset	uspto-grants-2011_09
ORD ID	ord-1598efeb7f48440da5f199a65c7531ba
Source note	uspto-grants-2011_09