Triethylamine → 3-Chloropyridine-2-carbonitrile

Compound 44A (2.59 g, 20 mmol), trimethylsilylcyanide (5.95 g, 60 mmol), Et3N (4.05 g, 40 mmol), and acetonitrile (20 mL) were combined in a 3-necked 250-mL round-bottomed flask under nitrogen and refluxed for 6 h, at which time HPLC analysis indicated complete consumption of starting material. The cooled reaction mixture was concentrated under reduced pressure to give a brown semi-solid which was partitioned between 3 N aqueous Na2CO3 and CH2Cl2. The organic layer was washed with water, brine, dried (MgSO4), filtered, and concentrated under reduced pressure. The residue was purified by flash chromatography using 5% Et2O/CH2Cl2 as eluent to give the product 44B as a white crystalline solid (1.84 g, 67%). 1H NMR (CDCl3) 7.37 (dd, J=4.7, 8.4 Hz, 1H), 7.73 (dd, J=1.4, 8.2 Hz, 1H), 8.47 (dd, J=1.3, 4.6 Hz, 1H); LC/MS m/z 139 [M+H]+.

1. temperaturerefluxed for 6 h, at which time HPLC analysis
2. customconsumption of starting material
3. customThe cooled reaction mixture
4. concentrationwas concentrated under reduced pressure
5. customto give a brown semi-solid which
6. customwas partitioned between 3 N aqueous Na2CO3 and CH2Cl2
7. washThe organic layer was washed with water, brine
8. dry with materialdried (MgSO4)
9. filtrationfiltered
10. concentrationconcentrated under reduced pressure
11. customThe residue was purified by flash chromatography

ORD record

ord-c79dedfd70c741d4af70eac0c8148be1

Source dataset

uspto-grants-2010_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07772267B2