반응 #474557

반응 방정식

5-Bromo-3-(2,2-dimethyl-1,1-dioxidotetrahydro-2H-thiopyran-4-yl)-1H-indole-7-carboxamide

1,4-dioxane

3-Thiopheneboronic acid

K2CO3

→

title compound

수율 19.3%

3-(2,2-Dimethyl-1,1-dioxidotetrahydro-2H-thiopyran-4-yl)-5-(3-thienyl)-1H-indole-7-carboxamide

수율 19.3%

용매

water

반응 조건

후처리

1. 1
   기타Argon was bubbled in the mixture for 10 min
2. 2
   기타argon was bubbled another 10 min
3. 3
   기타The vial is sealed
4. 4
   기타The reaction was evaporated
5. 5
   기타to remove most of the dioxane
6. 6
   기타The residue was partitioned between ethyl acetate and water
7. 7
   기타The layers were separated
8. 8
   건조the organic layer was dried (MgSO4)
9. 9
   기타the solvent was removed under vacuum
10. 10
    workup.DISSOLUTIONThe residue was dissolved in DMSO (3 mL)
11. 11
    기타was purified on a Gilson HPLC
12. 12
    농축The desired fractions were concentrated

실험 절차

5-Bromo-3-(2,2-dimethyl-1,1-dioxidotetrahydro-2H-thiopyran-4-yl)-1H-indole-7-carboxamide (144 mg, 0.36 mmol) was placed in a microwave vial and dissolved with 1,4-dioxane (6 mL) and water (3 mL). 3-Thiopheneboronic acid (92 mg, 0.72 mmol) and K2CO3 (150 mg, 1.1 mmol) were added. Argon was bubbled in the mixture for 10 min with stirring. PdCl2(dppf) (21 mg, 0.29 mmol) was added, and argon was bubbled another 10 min. The vial is sealed and heated in a microwave for 5 min at 100° C. on high absorption. The reaction was evaporated to remove most of the dioxane. The residue was partitioned between ethyl acetate and water. The layers were separated, the organic layer was dried (MgSO4), and the solvent was removed under vacuum. The residue was dissolved in DMSO (3 mL), and was purified on a Gilson HPLC. The desired fractions were concentrated, giving 28 mg (19%) of the title compound.

출처