1H-Pyrazole, 1-methyl- → HCID 57933026, compound

Participants

Role	Name	HCID	Charge
Reactant	1H-Pyrazole, 1-methyl-	HCID 70255	—
Reactant	3-(5-Bromo-3-methyl-thiophen-2-yl)-8-(1-ethyl-propyl)-2,6-dimethyl-imidazo[1,2-b]pyridazine	HCID 57932943	—
Reactant	Butyllithium	HCID 178418339	—
Catalyst	Zincchloride	HCID 3007855	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Product	HCID 57933026	HCID 57933026	88%

Reaction Steps

Using a procedure similar to Example 25, 1-methylpyrazole (0.17 g, 2.04 mmol), 1.56 M n-Bu-Li (1.34 mL, 2.09 mmol), ZnCl2 (4.3 mL, 2.14 mmol), 3-(5-bromo-3-methyl-thiophen-2-yl)-8-(1-ethyl-propyl)-2,6-dimethyl-imidazo[1,2-b]pyridazine (0.40 g, 1.02 mmol) and PdCl2(dppf) (0.037 g, 0.051 mmol) furnish the title compound (0.35 g, 0.89 mmol, 88%). 1H NMR (CDCl3), δ 0.88 (t, J=7.5 Hz, 6H), 1.74-1.92 (m, 4H), 2.17 (s, 3H), 2.50 (s, 3H), 2.52 (s, 3H), 3.28-3.38 (m, 1H), 4.05 (s, 3H), 6.42 (d, J=1.8 Hz, 1H), 6.68 (s, 1H), 7.08 (s, 1H), 7.46 (d, J=1.8 Hz, 1H). LC/MS (m/z): calcd. for C22H27N5S (M+H)+: 394.7; found: 394.2.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07612067B2
Source dataset	uspto-grants-2009_11
ORD ID	ord-aa0a99bbe16d428fb0dbe1c0709233f7
Source note	uspto-grants-2009_11