2-Chloropyridine-4-carboxylic acid tert-butyl ester

A solution of 10.0 g (63.4 mmol) 2-chloro-isonicotinic acid in 100 ml chloroform is heated to reflux temperature. In total 91.2 ml (380 mmol, 6 eq) N, N-dimethylformamide di-tert-butylacetal is added in 3 portions of each 30.4 ml at the start, after 1 h and after 2 h. After cooling to rt the mixture is diluted with EtOAc, washed with aq. bicarbonate and brine, and dried over sodium sulfate. The residue is purified by chromatography on silica (flashmaster, hexane to hexane/EtOAc 95/5) to give 7.6 g (35.6 mmol, 56percent) of the product as white solid.MS (LC/MS): 158=[M+H-tBu]a) To a solution of 2-chloroisonicotinic acid (5.00 g, 31.7 mmol) in toluene is added N, Ndimethylformamide di-tert. butylacetal (17.9 g, 79.3 mmol). The mixture is stirred at 90°C for 20 h. The mixture is concentrated, filtered and the filtrate is diluted with EA and washed with water, dried over MgSO4, filtered and concentrated. The crude product is purified by CC on silica gel eluting heptane:EA 5:1 to give tert. butyl 2-chloroisonicotinate (2.23 g, 33percent) as a colourless oil; LC-MS: tR = 0.98 mm, [M+1+CH3CN] = 255.31.To a solution of 1-methylpiperidine-4-thiol (XCIV) (200 mg, 1.52 mmol) in DMF (2 mL) was added NaH (61 mg, 1.53 mmol) at 0° C. stirred for 30 min. tert-Butyl-2-chloroisonicotinate (XC) (supplier: Synthonix) (400 mg, 1.87 mmol) was then added and the reaction mixture was stirred at room temperature overnight. The solvent was removed under vacuum and the residue was purified by silica gel column chromatography (24 g) (0'10percent 1.7N NH3 in MeOH/CHCl3) to produce tert-butyl 2-((1-methylpiperidin-4-yl)thio)isonicotinate (XCV) as an off-white solid (271 mg, 0.88 mmol, 57.7percent yield). ESIMS found for C16H24N2O2S m/z 309.2 (M+H).A solution of A solution of

Molecular Weight:213.66
XLogP3:2.4
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:3
Exact Mass:213.0556563
Monoisotopic Mass:213.0556563
Topological Polar Surface Area:39.2
Heavy Atom Count:14
Complexity:213
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes