1-[4-(CHLOROMETHYL)PHENYL]-1H-PYRAZOLE HYDROCHLORIDE

H) 1- [4- (chloromethyl) phenyl] -lH-pyrazole To a solution of [ 4- ( lH-pyrazol-l-yl ) phenyl] methanol (24.0 g) in 1 , 2-dichloroethane (200 mL) was added dropwise thionyl chloride (26.3 g) under ice-cooling, and the mixture was stirred at room temperature for 16 hr. The reaction mixture was concentrated under reduced pressure, and the residue was washed with tert-butyl methyl ether to give the title compound (23.5 g) . 1HNMR (400 MHz, CDC1Under a nitrogen stream, lithium chloride (0.32 g), zinc powder (0.50 g) and a stirrer bar were added to a reaction container, and the mixture was heated under reduced pressure at 180 C. for 15 min. After cooling to room temperature, the reaction container was filled with nitrogen, THF (2 mL) and 1, 2-dibromoethane (0.04 g) were added and the mixture was heated until air bubbles were developed. To the mixture was added trimethylsilyl chloride (0.02 g) and the mixture was stirred at 70 C. for 15 min. To the mixture was added Ethyl 7-methyl-6-(4, 4, 5 , 5-tetramethyl- [1, 3 , 2j dioxaborolan-2-yl)- 1 H-benzimidazole -4-carboxylate obtained in step 1 (0.1 g, 0.3 mmol) was dissolved in 5:1 mixture of 1, 4-dioxane and water (3.6 mL). Solid K2C03 (0.06 g, 0.42 mmol) and 1-(4-chloromethyl- phenyl)-1H-pyrazole (0.06 g, 0.31 mmol) were added. The reaction mixture was degassed with nitrogen for 15 minutes and [1, 1 t-bis(diphenyiphosphino)ferrocene]palladium(11) dichloride (24.7 mg. 0.03 rnrnol) was added. The reaction mixture was gradually heated toreflux temperature and was stirred at this temperature for 12 h. After cooling it to RT, the reaction mass was filtered through celite bed and the filtrate was evaporated under reduced pressure to obtain a crude product which was purified by silica gel column chromatography to obtain the title compound.Yield: 87.0 mg (80%); 'H - NMR (400 MHz, CDC13): oe 10.45 (bs, 1H), 8.12 (s, 1H), 7.89-7.88 (d, J=2.2 Hz, 2H), 7.87 (s, 1H), 7.61-7.59 (d, J=6.9 Hz, 2H), 7.24(d, J=6.5 Hz, 2H), 6.44 (s, 1H), 4.47 (q, 2H), 4.21 (s, 2H), 2.65 (s, 3H), 1.44 (t, J=7.1 Hz, 3H); (Mass (mlz): 361.1 (M+H).To a mixture of 1, 5-anhydro-2, 4-dideoxy-2-((2, 3-difluoro-4-methyl-5-(4, 4, 5, 5-tetramethyl-1, 3, 2-dioxaborolan-2-yl)benzoyl)amino)-L-threo-pentitol (0.0487 g) and DME (1.103 mL)/water (0.123 mL) were added A mixture of methyl 2-fluoro-3, 4-dimethyl-5-(4, 4, 5, 5-tetramethyl-1, 3, 2-dioxaborolan-2-yl)benzoate (0.51 g),

Molecular Weight:229.10
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:2
Exact Mass:228.0221037
Monoisotopic Mass:228.0221037
Topological Polar Surface Area:17.8
Heavy Atom Count:14
Complexity:155
Covalently-Bonded Unit Count:2
Compound Is Canonicalized:Yes