반응 #70789

반응 방정식

2,2′-bipyridine

NH4Cl

cyclopropylboronic acid

sodium carbonate

methyl 6-bromo-1H-indole-4-carboxylate

→

methyl 6-bromo-1-cyclopropyl-1H-indole-4-carboxylate

수율 71.7%

용매

1,2-dichloroethane

water

ethyl acetate

1,2-dichloroethane

반응 조건

후처리

1. 1
   기타In a oven dried 100 ml RBF
2. 2
   기타equipped
3. 3
   workup.STIRRINGThe solution was stirred for 15 min
4. 4
   workup.ADDITIONadded the hot suspension
5. 5
   기타to the reaction
6. 6
   온도Stopped heating after 6 h
7. 7
   추출Extracted with DCM (2×)
8. 8
   세척The combined organics were washed with brine
9. 9
   건조dried over magnesium sulfate
10. 10
    여과filtered
11. 11
    농축concentrated in vacuo
12. 12
    기타Purification of the residue by column chromatography (24 g Isco silica column

실험 절차

In a oven dried 100 ml RBF equipped, stir bar, septum and Nitrogen inlet was added methyl 6-bromo-1H-indole-4-carboxylate (0.508 g, 2.0 mmol) and 1,2-dichloroethane (7 mL). The solution was stirred for 15 min, then cyclopropylboronic acid (0.344 g, 4.00 mmol) and sodium carbonate (0.424 g, 4.00 mmol) were added. Diluted copper(II) acetate (0.363 g, 2.000 mmol) and 2,2′-bipyridine (0.312 g, 2.000 mmol) in 1,2-dichloroethane (12 mL), heated the mixture, and added the hot suspension to the reaction. The reaction was heated at 70° C. and monitored by LCMS. Stopped heating after 6 h and allowed to sit for 3 days at RT. Added to reaction saturated NH4Cl and water. Extracted with DCM (2×). The combined organics were washed with brine, dried over magnesium sulfate, filtered and concentrated in vacuo. Purification of the residue by column chromatography (24 g Isco silica column; gradient B: 3-25%. A:hexane. B: ethyl acetate) to give methyl 6-bromo-1-cyclopropyl-1H-indole-4-carboxylate (0.43 g, 1.433 mmol, 71.6% yield) as a yellow residue.

출처