5-Bromo-2-(1-methylethoxy)pyridine

Reference Example 17 AgC03 (1.3 g, 5 mmol), toluene (15 mL) and 2-iodopropane (1.2 mL, 12 mmol) were added to 5-bromopyridin-2(lm-one (1.74 g, 10 mmol). The mixture was stirred at 50 °C for 16 h, after which it was allowed to cool, then diluted with EtOAc and filtered through Celite(at). The filter cake was washed with EtOAc and the combined filtrates concentrated and purified by distillation to yield the sub-title compound (1.12 g, 52percent).To isopropanol (11 mL, 143 mmol) under nitrogen at 25° C. was added sodium hydride (95percent, 1.94 g, 76.7 mmol) portion wise over 5 minutes. The reaction was stirred for 16 hours and a solution of 2-fluoro-5-bromopyridine (9 g, 51 mmol) in N, N-dimethyl formamide (250 mL) was added over 10 minutes. The resulting mixture was heated at 130° C. for 4 hours and cooled to 25° C. The mixture was diluted with ether (500 mL, ) and washed with water (600 mL) and brine (300 mL). The organic layer was dried (MgSOGeneral procedure: 60percent NaH in oil (1.5:1, Sodium hydride:Mineral Oil, 5.20 g) was added in two portions to isopropyl alcohol (150 mL) at room temperature under NSynthesis of S-Methoxy-pyrrolidine-S-carboxylic acid r3-(6-isopropoxy-pyridin-3- VlH H-indazol-5-yll-amide In a 2-Propanol (i00 ml) NaH (2.73g, 68.2 mmol) was added slowly then the mixture was heated at 80 °C for ih. 5-bromo-2-fluoropyridine (5g, 28.4 mmol) was added and the resultant mixture was heated at 80 °C for further 1 5h. Reaction was monitored by TLC. The solvent was evaporated under vacuum, water was added in the residue and extractedwith ethyl acetate. The combined organic layer was washed with water, brine, dried overNa2SO4 and concentrated under vacuum to obtain title compound as an oil (5 g, 81 percent).1H NMR (400 MHz, Chloroform-d) 8.20 (d, J = 3.2 Hz, 1H), 7.64 (d, J = 8.7 Hz, 1H), 6.62 (dd, J= 8.7, 2.6 Hz, 1H), 5.26 (Quint, J= 6.6 Hz, 1H), 1.41 — 1.32 (d, 6H).

Molecular Weight:216.07
XLogP3:2.6
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:2
Exact Mass:214.99458
Monoisotopic Mass:214.99458
Topological Polar Surface Area:22.1
Heavy Atom Count:11
Complexity:119
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes