Sodium Chloride → HCID 59177869, compound

Temperature

-78 °C

A solution of 5.00 g (29.7 mmol) of methyl (2-fluorophenyl)acetate in 80 ml of THF is added dropwise to a 1 N solution of LiHMDS in hexane (35.7 ml, 35.7 mmol) cooled to −78° C. The mixture is stirred at −78° C. for 1 h and then 6.28 g (35.7 mmol) of 2-chloronicotinoyl chloride are added, and the mixture is stirred for a further hour. It is warmed to RT, and saturated ammonium chloride solution is added. The mixture is diluted with water and extracted with diethyl ether. The organic phase is dried over sodium sulfate and concentrated in vacuo. The residue is dissolved in 24 ml of DMSO, and 0.95 g (52.7 mmol) of water and 1.70 g (29.0 mmol) of sodium chloride are added. The solution is heated in 8 portions at 150° C. for 10 min in each case. It is then diluted with water and extracted with tert-butyl methyl ether. The organic phase is dried over sodium sulfate and concentrated in vacuo. The residue is purified by chromatography on silica gel (eluent: cyclohexane/ethyl acetate 2:1). 3.00 g (46% of theory) of the desired compound are obtained.

1. stirringthe mixture is stirred for a further hour
2. temperatureIt is warmed to RT
3. extractionextracted with diethyl ether
4. dry with materialThe organic phase is dried over sodium sulfate
5. concentrationconcentrated in vacuo
6. dissolutionThe residue is dissolved in 24 ml of DMSO
7. temperatureThe solution is heated in 8 portions at 150° C. for 10 min in each case
8. extractionextracted with tert-butyl methyl ether
9. dry with materialThe organic phase is dried over sodium sulfate
10. concentrationconcentrated in vacuo
11. customThe residue is purified by chromatography on silica gel (eluent: cyclohexane/ethyl acetate 2:1)

ORD record

ord-0ba940a3801943498810044529352193

Source dataset

uspto-grants-2012_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08309551B2