Iodoethane → HCID 59612943, compound

Temperature

0 °C

A solution of (2-amino-5-bromo-pyridin-3-yl)-methanol hydrobromide (Apollo, Cheshire, UK, 3.52 mmol) in DMF (15 ml) cooled with an ice-bath was treated with 55% NaH in oil (7.4 mmol) and the RM was stirred for 5 min at 0° C. and 30 min at rt, then was added iodoethane (3.87 mmol) and the RM was stirred for 1 h 15 min at rt. The RM was quenched with water and extracted with EtOAc. The organic layer was washed with saturated aqueous NaHCO3, with brine (2×), dried over Na2SO4, filtered and evaporated. The residue was taken in DMF and purified by preparative HPLC. The fractions containing product were basified with NaHCO3, concentrated and extracted with CH2Cl2 (2×). The combined organic layers were washed with brine, dried over Na2SO4, filtered, evaporated and dried under vacuum to give the title compound as a light yellow oil. (HPLC: tR 2.07 min (Method A); M+H=231, 233 MS-ES)

1. stirringthe RM was stirred for 1 h 15 min at rt
2. customThe RM was quenched with water
3. extractionextracted with EtOAc
4. washThe organic layer was washed with saturated aqueous NaHCO3, with brine (2×)
5. dry with materialdried over Na2SO4
6. filtrationfiltered
7. customevaporated
8. custompurified by preparative HPLC
9. additionThe fractions containing product
10. concentrationconcentrated
11. extractionextracted with CH2Cl2 (2×)
12. washThe combined organic layers were washed with brine
13. dry with materialdried over Na2SO4
14. filtrationfiltered
15. customevaporated
16. customdried under vacuum

ORD record

ord-98e4e668c2e342d3a298938a38b20b88

Source dataset

uspto-grants-2013_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08476294B2