2-Bromo-3,5-dimethylpyridine

2-[2-(3, 5-dimethylpyridin-2-yl)-5, 8-dioxo-6-(propan-2-yl)-5, 6, 7, 8-tetrahydro-4H-pyrazolo[1, 5-a]pyrrolo[3, 4-d]pyrimidin-4-yl]-N-(5-fluoropyridin-2-yl)acetamide . A mixture of j0209] Under nitrogen condition, 2-bromine-3, 5-dimethyl pyridine (500.00 mg, 2.69 mmol, 1.00 eq) and WX1313-3-1 (592.07 mg, 2.96 mmol, 1.10 eq) were dissolved in methylbenzene (25 ml). Tris(dibenzylideneacetone)dipalladium (246.10 mg, 269.00 tmol, 0.10 eq), sodium tert-butoxide (387.40 mg, 4.04 mmol, 1.50 eq) and 1, 1?-binaphthyl-2, 2?- bis (diphenylphosphino) (335.00 mg, 538.00 tmol, 0.20 eq) were added. The mixture was stirred at 90 C. for 18 h. After reaction, the reaction liquid was filtered through diatomite to remove the palladium catalyst, the filter cake was washed with ethyl acetate (10 ml), the solvent was dried by rotary evaporation under vacuum, and ethyl acetate (30 ml) was added. Then the resulting mixture was washed with water (10 ml), the methyl acetate phase was dry-spined under vacuum, and the crude was purified by column chromatography (ethyl acetate:petroleum ether=1.-20%) to obtain WXO12-1 (Rf=0.5). 'H NMR (400 MHz, CDC13) oeppm:7.74 (s, 1H), 6.99 (s, 1H), 4.08-4.02 (m, 1H), 3.98 (br, s, 1H), 3.60-3.57 (m, 1H), 3.30-3.38 (m, 2H), 3.29-3.24 (m, 1H), 2.07 (s, 3H), 1.97 (s, 3H), 1.84-1.82 (m, 1H), 1.71-1.60 (m, 2H), 1.49-1.43 (m, 1H), 1.33 (s, 9H).In a three-neck round-bottom flask were placed 2-bromo-3, 5- dimethylpyridine (5.00 g, 26.87 mmol) and dry THF (40 mL) under N2 atmosphere. The solution was cooled down at -78C. nBuLi 2.5 M in hexanes (12.89 mL, 32.25 mmol) was added dropwise to the solution. The reaction mixture was stirred at -78C for 20 mm and 5-methylfuran-2-carbaldehyde (2.94 mL, 29.56 mmol) dissolved in dry THF (10 mL) was added dropwise to thesolution. The reaction mixture was stirred at -78C for 30 mm and then was slowly warmed to rt and the stirring was kept at this temperature overnight. The reaction was quenched with sat. NH4CI. The aqueous layer was extracted with EtOAc. The combined organic layers were dried over Mg504, filtered and the solution was concentrated to dryness. The crude material was purified by silica gel column chromatography eluting with a gradient of Hexanes/EtOAc from [96:4] to [90:10]. The product fractions were collected and evaporated under redcued pressure to afford (3, 5-di methyl pyrid in-2-yl)(5-methylfu ran-2- yl)methanol Ex.87a (3.29 g, 56%) as orange oil. 1 H NMR (400 MHz, CDCI3, d in ppm): 2.13 (s, 3H), 2.24 (d, 3H, J=0.8Hz), 2.33 (s, 3H), 5.71 (s, 1H), 5.83-5.86

Molecular Weight:186.05
XLogP3:2.6
Hydrogen Bond Acceptor Count:1
Exact Mass:184.98401
Monoisotopic Mass:184.98401
Topological Polar Surface Area:12.9
Heavy Atom Count:9
Complexity:94.9
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes