1,3-Dichloroacetone → HCID 19367122, compound

Temperature

80 °C

A mixture of 2-amino-5-methoxypyridine (0.5036 g; prepared by the method of Lombardino, J. Med. Chem. 1981, 24 39-42), 1,3-dichloroacetone (Aldrich; 0.3935 g), and dimethoxyethane (2.5 mL) is stirred overnight at room temperature. The mixture is concentrated under reduced pressure and ethanol (7.9 mL) is added. After the mixture has stirred for 30 min at 80° C., it is cooled and concentrated under reduced pressure. The residue is partitioned between dichloromethane and saturated aq. sodium bicarbonate and the combined organic layers are dried with MgSO4 and concentrated under reduced pressure. The residue is chromatographed on silica gel using methanol/dichloromethane (4/96) to give 0.1392 g of 2-(chloromethyl)-6-methoxyimidazo[1,2-a]pyridine; 1H NMR (CDCl3) δ 3.82, 4.75, 6.99, 7.48, 7.56, 7.59.

1. customprepared by the method of Lombardino, J
2. concentrationThe mixture is concentrated under reduced pressure and ethanol (7.9 mL)
3. additionis added
4. temperatureit is cooled
5. concentrationconcentrated under reduced pressure
6. customThe residue is partitioned between dichloromethane and saturated aq. sodium bicarbonate
7. dry with materialthe combined organic layers are dried with MgSO4
8. concentrationconcentrated under reduced pressure
9. customThe residue is chromatographed on silica gel

ORD record

ord-88fae60c51154777a3ecc6f731d72227

Source dataset

uspto-grants-2000_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06013654