Water → 2-(2-Furanyl)-5-methanesulfonylindole

Temperature

60 °C

To a suspension of the compound obtained in Example 8 (5) (2.00 g), bistriphenylphosphine palladium dichloride (321 mg), cuprous iodide (87.0 mg) and triethylamine (1.38 g) in N,N-dimethylformamide (46 ml), a solution of 2-ethynylfuran (842 mg) in N,N-dimethylformamide (46 ml) was slowly added dropwise under nitrogen atmosphere and the mixture was stirred at 60° C. for 3 hours. The reaction solution was then poured into water, extracted with chloroform, washed with a saturated aqueous NaCl solution, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The resulting residue was separated using silica gel column chromatography (methanol:chloroform=1:100). To a solution of the obtained colorless amorphous compound (1.10 g) in methanol (28 ml) was added a 1N aqueous potassium hydroxide solution (5.52 ml) and the mixture was stirred at 60° C. for 1 hour. After completion of the reaction, the reaction solution was concentrated under reduced pressure. The resulting residue was poured into water, extracted with chloroform, washed with a saturated aqueous NaCl solution, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The resulting residue was separated using silica gel preparative thin-layer chromatography (methanol chloroform=1:20) to obtain 350 mg of the desired product as a brown crystal.

1. extractionextracted with chloroform
2. washwashed with a saturated aqueous NaCl solution
3. dry with materialdried over anhydrous sodium sulfate
4. filtrationfiltered
5. concentrationconcentrated under reduced pressure
6. customThe resulting residue was separated
7. additionTo a solution of the obtained colorless amorphous compound (1.10 g) in methanol (28 ml) was added a 1N aqueous potassium hydroxide solution (5.52 ml)
8. stirringthe mixture was stirred at 60° C. for 1 hour
9. customAfter completion of the reaction
10. concentrationthe reaction solution was concentrated under reduced pressure
11. additionThe resulting residue was poured into water
12. extractionextracted with chloroform
13. washwashed with a saturated aqueous NaCl solution
14. dry with materialdried over anhydrous sodium sulfate
15. filtrationfiltered
16. concentrationconcentrated under reduced pressure
17. customThe resulting residue was separated

ORD record

ord-626deb9df2e84658842ac908543ebf04

Source dataset

uspto-grants-2009_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07612070B2