Cesium carbonate → HCID 59263396, compound

A mixture of 2-bromothiazole-5-methanol (0.80 g, 4.12 mmol) in thionyl chloride (10 mL) was refluxed for 3 h, and the mixture was evaporated to dryness and dried in vacuo. The residue was re-dissolved in 2-butanone (15 mL), followed by addition of cesium carbonate (2.61 g, 8.0 mmol) and spiro[furo[2,3-f][1,3]benzodioxole-7,3′-indol]-2′(1′H)-one (1.12 g, 4.0 mmol). The reaction mixture was refluxed for 16 h, then concentrated to dryness in vacuo. The residue was taken up in ethyl acetate (200 mL), washed by water (50 mL) and brine (50 mL). The organic phase was dried over sodium sulfate, filtered, and the filtrate was concentrated to dryness. The residue was purified by flash chromatography with 25% ethyl acetate in hexanes to afford 1′-[(2-chloro-1,3-thiazol-5-yl)methyl]spiro[furo[2,3-f][1,3]benzodioxole-7,3′-indol]-2′(1′H)-one (0.70 g, 38%) as a colorless solid: 1H NMR (300 MHz, CDCl3) δ 7.58 (s, 1H), 7.30 (ddd, J=7.5, 7.5, 1.2 Hz, 1H), 7.22-7.17 (m, 1H), 7.09 (ddd, J=7.5, 7.5, 0.9 Hz, 1H), 6.91 (d, J=7.8 Hz, 1H), 6.52 (s, 1H), 6.09 (s, 1H), 5.90-5.86 (m, 2H), 5.16-5.08 (m, 1H), 4.97 (d, J=15.9 Hz, 1H), 4.92 (d, J=9.0 Hz, 1H), 4.66 (d, J=9.0 Hz, 1H); MS (ES+) m/z 413.0 (M+1), 415.0 (M+1).

1. temperaturewas refluxed for 3 h
2. customthe mixture was evaporated to dryness
3. customdried in vacuo
4. dissolutionThe residue was re-dissolved in 2-butanone (15 mL)
5. temperatureThe reaction mixture was refluxed for 16 h
6. concentrationconcentrated to dryness in vacuo
7. washwashed by water (50 mL) and brine (50 mL)
8. dry with materialThe organic phase was dried over sodium sulfate
9. filtrationfiltered
10. concentrationthe filtrate was concentrated to dryness
11. customThe residue was purified by flash chromatography with 25% ethyl acetate in hexanes

ORD record

ord-8d4eb05c89e94d1faab0e30bdbef9ffb

Source dataset

uspto-grants-2012_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08263606B2