3-CHLORO-6-CYCLOPROPYLPYRIDAZINE

General procedure: A flask is charged with halogeno aryl derivative (1 eq.), dioxane previously degassed with N2, ELpim (1.1 to 1.5 eq.), potassium acetate (3 to 4 eq.) and Pd(dppf)Cl2-DCM (0.1 to 0.12 eq.). The mixture is stirred to 90 C-l 10 C for 1.5 h-20 h, cooled to RT or 50 C and used as such in the Suzuki coupling (cf. El .3 using from 0.9 to 1.4 eq. of arylbromide or arylchloride).General procedure: Under an inert atmosphere, 5-bromo-2-chloropyrimidine (10 g, 0.051 mol), and cesium carbonate (60 g, 0.18 mol) were dispersed in a 95/5 w mixture of toluene and water (400 mL). This was degassed by gently bubbling argon in the reaction and [Iota, Gamma- bis(diphenylphosphino)ferrocene] dichloropalladium complexed with dichloromethane (2.1 g, 0.0025 mol) and cyclopropylboronic acid (5.3 g, 0.062 mol) were added. The flask was heated to reflux for 20 minutes, upon cooling the suspension was diluted in ethyl acetate, the filtered organic layer was washed with water, brine, dried over magnesium sulfate and concentrated to dryness. The residue was purified by a chromatography over silica gel (cyclohexane - ethyl acetate 6/1) to yield the pyrimidine as a white powder (5.3 g, 69 %; stored at -20 C). (CDCI3): 0.79 (m, 2H); 1.13 (m, 2H); 1.88 (m, 1H); 8.36 (s, 2H). 3C (CDCI3): 9.0; 10.3; 135.7; 157.3; 158.5. HRMS: Calc. for C7H7C1N2 + H: 155, 0376; Found: 155.0370.General procedure: In a reaction vial designed for microwave heating, the considered alkoxypyrazole (2 mmol), the considered halogenated heteroaryl (2.2 mmol) and cesium carbonate (2.8 mmol) were stirred in dimethylformamide or acetonitrile (3 mL) as specified in the examples. This was heated using a microwave at a temperature between 120 C and 180 C for the individually specified duration. The resulting suspension was diluted in water, extracted with ethyl acetate and the organic layer was washed with brine, dried over magnesium sulfate and concentrated to dryness. The residue was further purified as described below.

Molecular Weight:154.60
XLogP3:1.4
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:1
Exact Mass:154.0297759
Monoisotopic Mass:154.0297759
Topological Polar Surface Area:25.8
Heavy Atom Count:10
Complexity:125
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes