반응 #995474

반응 방정식

6-bromoindolin-2-one

N-(6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)naphthalen-2-yl)thiophene-3-carboxamide

K2CO3

1,4-dioxane

→

title compound

수율 16.0%

N-(6-(2-oxoindolin-6-yl)naphthalen-2-yl)thiophene-3-carboxamide

수율 16.0%

용매

water

반응 조건

후처리

1. 1
   workup.ADDITIONwas added
2. 2
   기타The reaction tube was sealed
3. 3
   온도heated in the microwave (CEM microwave) at 60 Watts and 80 C, first for 10 minutes
4. 4
   추출extracted with dichloromethane (3×10 ml) and EtOAc (6×10 ml)
5. 5
   건조dried over sodium sulfate
6. 6
   여과filtered
7. 7
   농축concentrated
8. 8
   기타purified on HPLC (10%->95% MeCN/water with 0.1% TFA)

실험 절차

6-bromoindolin-2-one (25.2 mg, 0.119 mmol), N-(6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)naphthalen-2-yl)thiophene-3-carboxamide (72.1 mg, 0.190 mmol), Fibercat palladium catalyst (Johnson-Matthey, 35.4 mg), and K2CO3 (2 M in water, 0.25 ml, 0.5 mmol) were combined in a microwave reaction vessel and 1,4-dioxane (1.1 ml) was added. The reaction tube was sealed and heated in the microwave (CEM microwave) at 60 Watts and 80 C, first for 10 minutes, and then for 20 minutes. The reaction was cooled to room temperature, diluted with water (5 ml), and extracted with dichloromethane (3×10 ml) and EtOAc (6×10 ml). The organic extracts were combined, dried over sodium sulfate, filtered, concentrated, and purified on HPLC (10%->95% MeCN/water with 0.1% TFA) to afford title compound (7.1 mg, 16%). MS (ESI pos. ion) m/z: 385 (M+H). Calc'd Exact Mass for C23H16N2O2S: 384.

출처