1,1'-Carbonyldiimidazole → HCID 3616760, compound

To a stirred suspension of 1H-Indole-6-carboxylic acid (5.65 g, 35.1 mmol) in 55 mL of THF was added 1,1′-carbonyldiimidazole (6.25 g, 38.6 mmol). The suspension was stirred for 2 h at room temperature followed by addition of O,N-dimethyl-hydroxylamine hydrochloric acid (4.10 g, 42.1 mmol) in an ice-bath. The mixture ws stirred at room temperature overnight. The mixture was extracted with EtOAc (2×50 mL). The combined EtOAc extracts were washed brine (50 mL), dried over MgSO4, filtered and concentrated to an oil, which was purified by flash column chromatography (EtOAc/Hexane) to give 1H-Indole-6-carboxylic acid methoxy-methyl-amide as an oil (5.54 g, 77% yield): 1H NMR (CDCl3) δ 3.39 (s 3H, NCH3), 3.58 (s, 3H, OCH3), 6.55-6.57 (m, 1H, Ar), 7.29-7.84 (m, 4H, Ar), 8.85 (brs, 1H, NH). The product was used in the next step without further purification.

1. stirringThe mixture ws stirred at room temperature overnight
2. extractionThe mixture was extracted with EtOAc (2×50 mL)
3. washThe combined EtOAc extracts were washed brine (50 mL)
4. dry with materialdried over MgSO4
5. filtrationfiltered
6. concentrationconcentrated to an oil, which
7. customwas purified by flash column chromatography (EtOAc/Hexane)

ORD record

ord-b9820f10b3ff4ac4a6f1381b794d69d0

Source dataset

uspto-grants-2008_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07468446B2