Triethylamine → HCID 57791832, compound

(6-bromo-3-oxo-1,3-dihydroisobenzofuran-1-yl)triphenylphosphonium bromide (95) (9.0 g, 16.24 mmol) and 2-fluoro-5-formylbenzonitrile (2.91 g, 19.49 mmol) were dissolved DCM (60 mL), to this was added triethylamine (2.94 mL, 21.11 mmol) and the reaction was stirred overnight. The reaction mixture was quenched with water (50 mL), extracted with DCM (2×75 mL), the organic layer was dried over MgSO4, filtered and evaporated to afford an orange gum. This was passed through a plug of silica eluting with ethyl acetate to afford a yellow gum. To this was added water (40 mL), EtOH (40 mL) and DMF (4 mL). Hydrazine hydrate (8.13 g, 162.39 mmol) was added and the reaction was heated at reflux overnight. The reaction was cooled and the precipitate was collected by filtration, washed with EtOH (25 mL) and air dried to afford the desired compound as a white solid (2.410 g, 41.4% yield), which was used without further purification; 1H NMR (400.132 MHz, DMSO) δ 4.38 (2H, s), 7.48 (1H, t), 7.75-7.71 (1H, m), 7.89 (1H, dd), 8.02 (1H, d), 8.18 (1H, d), 8.22 (1H, s), 12.64 (1H, s); m/z (LC-MS, ESI−), RT=2.18 (M−H 358).

1. customThe reaction mixture was quenched with water (50 mL)
2. extractionextracted with DCM (2×75 mL)
3. dry with materialthe organic layer was dried over MgSO4
4. filtrationfiltered
5. customevaporated
6. customto afford an orange gum
7. customto afford a yellow gum
8. temperaturethe reaction was heated
9. temperatureat reflux overnight
10. temperatureThe reaction was cooled
11. filtrationthe precipitate was collected by filtration
12. washwashed with EtOH (25 mL) and air
13. customdried

ORD record

ord-01df70d74ca548b6b2abffeb9a922eae

Source dataset

uspto-grants-2012_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08129380B2