1H-imidazole-2-carbaldehyde → HCID 62222276, compound

Temperature

80 °C

To a solution of the 2-imidazolecarboxaldehyde (545 mg, 5.67 mmol) and 2-(bromomethyl)pyridine hydrobromide (1.58 g, 6.24 mmol) in DMF (20 mL) was added N,N-diisopropylethylamine (3.0 mL, 17.01 mmol). The reaction mixture was heated to 80° C. overnight. Then it was cooled and quenched with saturated NaHCO3 (20 mL). It was extracted with CH2Cl2 (c×20 mL). The combined organic layers were washed with brine (20 mL), dried (MgSO4), filtered, concentrated, and dried in vacuo to afford a dark brown oil. Purification by flash column chromatography on silica gel using 1% →2% CH3OH/CH2Cl2 afforded the product as a yellow solid (397 mg, 37%). 1H NMR (CDCl3) δ 5.71 (s, 2H), 7.18-7.24 (m, 2H), 7.32 (s, 1H), 7.36 (s, 1H), 7.65 (td, 1H, J=10.4, 1.5 Hz), 8.56 (d, 1H, J=4.5 Hz), 9.82 (s, 1H).

1. temperatureThen it was cooled
2. customquenched with saturated NaHCO3 (20 mL)
3. extractionIt was extracted with CH2Cl2 (c×20 mL)
4. washThe combined organic layers were washed with brine (20 mL)
5. dry with materialdried (MgSO4)
6. filtrationfiltered
7. concentrationconcentrated
8. customdried in vacuo
9. customto afford a dark brown oil
10. customPurification by flash column chromatography on silica gel using 1% →2% CH3OH/CH2Cl2

ORD record

ord-8ecbd39fbfa844c78a647afa88ee7536

Source dataset

uspto-grants-2008_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07354934B2