2-CHLOROPYRIDINE-5-ACETIC ACID ETHYL ESTER

To a solution of EtOH (27 mL), concentrated H2SOStep 2. Synthesis of (6-chloropyridin-3-yl) acetic acid ethyl ester. 10 g (65 5 mmol) (6-chloropyrιdιn-3-yl)acetonιtrιle were added to a mixture of 122 mL ethanol and 46 mL cone sulfuric acid and the mixture stirred under reflux for 5 h After cooling to ambient temperature, the reaction mixture was slowly added dropwise. while stirring, to a mixture of 161 g sodium bicarbonate and 450 mL water The aqueous phase was extracted with DCM (three times with 300 mL each time) The combined organic phases were dried over sodium sulfate, filtered and concentrated on a rotary evaporator The crude oil was purified by silica gei chromatography, eluted using a gradient of 2/98(v/v) EtOAc/hexanes to 9/91 (v/v) EtOAc/hexanes to afford 9 8 g (75percent) of product as clear oil ESI-MS m/z 200 (MH)15.2 g 2-chloropyridin-5-ylacetonitrile was added to a 250 ml four-mouthed flask. Add 150 ml ethanol. 10ml 98percent concentrated sulfuric acid. Heat to reflux. Reflux reaction for 4 hours, reaction finishes, prolapsed ethanol, add 100 g water to stir, is neutral pH the sodium carbonate is used to regulate, filter, to obtain 2-chloro pyridine ethyl acetate 13 g.To a solution of 6-chloro-3-pyridineacetic acid (1 g, 5.83 mmol) in ethanol was added sulfuric acid (1.6 ml_). The mixture was refluxed for 4 h, then cooled to room temperature and concentrated. The residue was diluted with ethyl acetate and washed with a saturated sodium hydrogen carbonate solution. The resulting mixture was dried over MgS0To a solution of 6-chloro-3-pyridineacetic acid (1 g, 5.83 mmol) in ethanol was added sulfuric acid (1.6 ml_). The mixture was refluxed for 4 h, then cooled to room temperature and concentrated. The residue was diluted with ethyl acetate and washed with a saturated sodium hydrogen carbonate solution. The resulting mixture was dried over magnesium sulphate and concentrated under reduced pressure to afford crude which was purified by column chromatography to afford ethyl 2-(6-chloropyridin-3-yl)acetate (1.1 g, 95 percent).Step 1: Step 1:[0815]To a solution of 6-chloro-3-pyridineacetic acid (1 g, 5.83 mmol) in ethanol was added sulfuric acid (1.6 mL). The mixture was refluxed for 4 h, then cooled to room temperature and concentrated. The residue was diluted with ethyl acetate and washed with a saturated sodium hydrogen carbonate solution. The resulting mixture was dried over magnesium sulfate and concentrated under reduced pressure to afford crude which was purified by column chromatography to afford ethyl 2-(6-chloropyridin-3-yl)acetate (1.1 g, 95percent).Example 28. Synthesis of K002. To a suspension of 6-cholro-2-pyridineacetic acid methyl ester (10 g, 58.2 mmol) was added cone, sulfuric acid (30 mL) and the reaction was heated to 70 °C for 4 hr. The reaction mixture was cooled to room temperature and concentrated and the resulting residue was suspended in HSynthesis of compound 74.2. To a solution of compound 74.1 (lOg, 0.0584mol, l .Oeq.) in ethanol (100 mL) was added drop wise H

Molecular Weight:199.63
XLogP3:2
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:4
Exact Mass:199.0400063
Monoisotopic Mass:199.0400063
Topological Polar Surface Area:39.2
Heavy Atom Count:13
Complexity:175
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes