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, 1 H), 7.73 (dd, J=1.4, 8.2 Hz, 1 H), 8.47 (dd, J=1.3, 4.6 Hz, 1 H); 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レコード

ord-86e76248edb0460188ba508c4c128e78

出典データセット

uspto-grants-2008_07

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US07405234B2