4-Iodo-2-methylpyridine

4-Chloropicoline (10 g, 78 mmol), sodium iodide (17.8 g, 118 mmol) and hydroiodic acid (57percent, 26 mL, 196 mmol) were heated in a sealed class tube at 140C for 7 days. The reac- tion mixture was poured into ice water and neutralized by addition of sodium hydroxide. This mixture was extracted three times with dichloromethane (300 mL each). The com- bined organic extracts were dried with magnesium sulfate, filtered and evaporated. The desired product was obtained as an off-white solid (14.7 g, 85percent) and used without any further purification for the next step.4-Iodo-2-methylpyridine and (4-IODO-2-PYRIDYL) methylacetate : 2- ( ( (TETT-BUTYLDIMETHYLSILYL) OXY) METHYL)-4-CHLOROPYRIDINE (600 mg, 2.33 MMOL), dry sodium iodide (5 g) and freshly distilled acetyl chloride (0. 7. mL, 9.78 MMOL) in 6 mL of anhydrous ACETONITRILE were REFLUXED under nitrogen for 33 hours. Aqueous 10percent K2CO3/5percent NAHSO3 was added and the mixture extracted three times with chloroform. After drying (NA2SO4) and evaporation of the chloroform, flash chromatography (hexane/EtOAc 9 : 1) yielded 110 mg (22percent) of 4-Iodo-2- METHYLPYRIDINE as a white solid and 290 mg (45percent) of (4-iodo-2-pyridyl) methylacetate as a white solid. 4-Iodo-2-methypyridine: 1H NMR (CHO) 8 8.06 (d, LH, *5. 2 Hz, H-6); 7.48 (d, 1H, J=1.1 Hz, H- 3); 7.38 (dd, 1H, J1=5. 2, 1. 4 Hz, H-5); 2.41 (s, 3H, CH3) ;13C NMR (CDCl3) 8 159.8 (C-2), 149.8 (C-6), 133.0 (C-3), 130.4 (C-5), 106.3 (C-4), 24.5 (CH3). (4-iodo-2-pyridyl) METHYLACETATE : 1H NMR (CDCl3) 8 8.16 (d, 1H, J=5. 2 Hz, H-6); 7.66 (d, LH, J=1. 0 Hz, H-3); 7.54 (dd, 1H, J1=5. 2, . J2=1. 6 Hz, H-5); 5.09 (s, 2H, CH2) ; 2.11 (s, 3H, CH3) ; 13C NMR (CDCTS) 8 170.9 (CO), 157.1 (C-2), 150.1 (C-6), 132.5 (C-3), 131.3 (C-5), 106.6 (C-4), 66.3 (CH2), 21.3 (CH3).Weigh 4.2 g of diosgenin in 200 mL of dichloromethane in a 500 mL three-necked flask, add 1.8 g of sodium tert-butoxide and 2.5 g of 2-methyl-4-iodo-pyridine, stir, react at room temperature for 24 h, Agent: petroleum ether-ethyl acetate (1: 1), developer: 5% ethanol solution of phosphomolybdic acid). Test the total reaction of diosgenin, evaporate under reduced pressure to a volume of 20 mL, cool to 5 C and crystallize overnight, filter TLC followed the process of separation and purification of the reaction and the product. The solid was dried at 60 C. for 4 h to obtain 4.0 g of the product as a light yellow powder.[253] 1H-pyrazol-3-amine (300 mg, 3.61 mmol), A suspension of (R)-l-(l-(4-fluorophenyl)ethyl)-3-(lH-pyrazolo[3, 4-c]pyridin-5- yl)urea (40 mg, 0.13 mmol), Intermediate VII (5-Chloro-l-(2-methylpyridin-4-yl)-lH-pyrazolo[3, 4-c]pyridin-7-yl)methanol Step 1 : 7-(((tert-Butyldimethylsilyl)oxy)methyl)-5-chloro-l-(2-methylpyridin-4-yl)-lH- pyrazolo[3, 4-c]pyridine. To a solution of 7-(((tert-butyldimethylsilyl)oxy)methyl)-5-chloro-lH- pyrazolo[3, 4-c]pyridine (1 g, 3.36 mmol) in DMF (20 mL) were added

Molecular Weight:219.02
XLogP3:1.9
Hydrogen Bond Acceptor Count:1
Exact Mass:218.95450
Monoisotopic Mass:218.95450
Topological Polar Surface Area:12.9
Heavy Atom Count:8
Complexity:74.9
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes