Methanol → (E)-4-(2-(2-(Quinolin-2-yl)vinyl)imidazo[1,2-b]pyridazin-8-yl)morpholine

Participants

Role	Name	HCID	Charge
Reactant	Methanol	HCID 887	—
Reactant	2-Methylquinoline	HCID 7060	—
Reactant	Bromotrimethylsilane	HCID 76113	—
Reactant	8-Morpholinoimidazo[1,2-b]pyridazine-2-carbaldehyde	HCID 117728638	—
Solvent	Dimethylformamide	HCID 6228	—
Product	(E)-4-(2-(2-(Quinolin-2-yl)vinyl)imidazo[1,2-b]pyridazin-8-yl)morpholine	HCID 117728366	—

Reaction Conditions

Temperature	80 °C

Reaction Steps

To a solution of compound 5e (10 g, 43 mmol) and 2-methylquinoline (4.6 g, 32 mmol) in DMF (10 mL) was added TMSBr (2.9 g, 19 mmol) dropwise. The reaction mixture was stirred at 80° C. for 2 h. MeOH (10 mL) was added. The solids formed were collected by filtration and washed with Et2O (2×50 mL) to obtain compound 57c as a yellow solid. Mass Spectrum (LCMS, ESI pos.): Calcd. for C21H19N5O: 358.2 (M+H). Found: 358.3.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09193736B2
Source dataset	uspto-grants-2015_11
ORD ID	ord-20a174ab630244f0a5b32e76b9f2bde3
Source note	uspto-grants-2015_11