Iodine → HCID 21471444, compound

Temperature

110 °C

A mixture of 3-Ethynyl-2-(4-fluorophenyl)-4-(1-methylethyl)-quinoline (1.000 gm, 3.64 mmol) (the preparation of which is described in Example 5) and AIBN (13 mg) in 140 ml of tri-n-butylstannyl hydride was rapidly heated to 110° C. After 5 minutes of heating, the mixture was treated with additional Bu3SDE (0.4 ml) and the temperature of the reaction was raised to 130° C. Approximately 10 mg of AIBN was added to the reaction mixture every 0.5 hours. After 4.5 hours, the mixture was cooled to room temperature, diluted with Et2O (25 ml) and treated with solid I2 (3.08 gm, 12.2 mmol). The dark reaction mixture was stirred for 1 hour, then quenched with 10% Na2SO3 in saturated NaHCO3. The layers were shaken and separated. The ethereal layer was washed with brine, dried (Na2SO4), filtered and stripped to yield a yellow oil which was triturated with cold hexane to give a precipitate. Recrystallization of the solid from hot hexane gave 1.438 gm (E)-2-(4-Fluorophenyl)-3-(2-iodoethenyl)-4-(1-methylethyl)quinoline (917 mg, 64%) as light yellow crystals.

1. customthe preparation of which
2. temperatureAfter 5 minutes of heating
3. additionthe mixture was treated with additional Bu3SDE (0.4 ml)
4. temperaturethe temperature of the reaction was raised to 130° C
5. temperaturethe mixture was cooled to room temperature
6. customThe dark reaction mixture
7. customquenched with 10% Na2SO3 in saturated NaHCO3
8. stirringThe layers were shaken
9. customseparated
10. washThe ethereal layer was washed with brine
11. dry with materialdried (Na2SO4)
12. filtrationfiltered
13. customto yield a yellow oil which
14. customwas triturated with cold hexane
15. customto give a precipitate
16. customRecrystallization of the solid from hot hexane

ORD record

ord-cdc54e7b59db41daa79d2a271cc99b81

Source dataset

uspto-grants-1997_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05691322