반응 #172221

반응 방정식

5-(3,4,5-trimethoxyphenyl)-1-((2-(trimethylsilyl)ethoxy)-methyl)-1H-pyrrolo[2,3-b]pyridin-2(3H)-one

cesium carbonate

methyl iodide

→

title compound

수율 73.1%

3,3-dimethyl-5-(3,4,5-trimethoxyphenyl)-1H-pyrrolo[2,3-b]pyridin-2(3H)-one

수율 73.1%

용매

DMF

반응 조건

후처리

1. 1
   기타after which it was partitioned between EtOAc and H2O
2. 2
   기타The organic layer was separated
3. 3
   건조dried over MgSO4
4. 4
   여과filtered
5. 5
   농축concentrated in vacuo
6. 6
   workup.DISSOLUTIONThe residue was dissolved in 6 N HCl (10 mL)
7. 7
   workup.STIRRINGMeOH (5 mL), and the resulting mixture was stirred at room temperature overnight
8. 8
   기타after which it was partitioned between EtOAc and H2O
9. 9
   농축The organic layer was concentrated in vacuo
10. 10
    workup.DISSOLUTIONthe residue was dissolved in EtOH (2 mL)
11. 11
    workup.ADDITIONPotassium acetate (100 mg) was then added
12. 12
    workup.STIRRINGthe reaction was stirred for 2 hr
13. 13
    기타The resulting solution was purified via preparatory HPLC

실험 절차

To a solution of 5-(3,4,5-trimethoxyphenyl)-1-((2-(trimethylsilyl)ethoxy)-methyl)-1H-pyrrolo[2,3-b]pyridin-2(3H)-one (43 mg, 0.10 mmol) in DMF (2 mL) was added cesium carbonate (0.17 g, 0.50 mmol) and methyl iodide (19 μL, 0.30 mmol). The resulting solution was stirred for 48 hr at room temperature, after which it was partitioned between EtOAc and H2O. The organic layer was separated, dried over MgSO4, filtered, and concentrated in vacuo. The residue was dissolved in 6 N HCl (10 mL) and MeOH (5 mL), and the resulting mixture was stirred at room temperature overnight, after which it was partitioned between EtOAc and H2O. The organic layer was concentrated in vacuo, and the residue was dissolved in EtOH (2 mL). Potassium acetate (100 mg) was then added, and the reaction was stirred for 2 hr. The resulting solution was purified via preparatory HPLC to give the title compound (24 mg, 73%). 1H NMR (CDCl3, 300 MHz): δ 9.72 (s, 1H), 8.35 (d, J=2.1 Hz, 1H), 7.60 (d, J=1.8 Hz, 1H), 6.71 (s, 2H), 3.95 (s, 6H), 3.90 (s, 3H), 1.49 (s, 6H). HPLC retention time: 1.80 minutes; MS ESI (m/z): 329.4 (M+1)+, calc. 328.

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