Sodium Methoxide → 4-Methoxy-1-[[2-(Trimethylsilyl)ethoxy]methyl]-1H-pyrrolo[2,3-b]pyridine-5-carbaldehyde

HRID 2199324노트

반응식

HRID 2199324 반응식
Cl[C:2]1[C:7]([CH:8]=[O:9])=[CH:6][N:5]=[C:4]2[N:10]([CH2:13][O:14][CH2:15][CH2:16][Si:17]([CH3:20])([CH3:19])[CH3:18])[CH:11]=[CH:12][C:3]=12.[CH3:21][O-:22].[Na+]>CO>[CH3:21][O:22][C:2]1[C:7]([CH:8]=[O:9])=[CH:6][N:5]=[C:4]2[N:10]([CH2:13][O:14][CH2:15][CH2:16][Si:17]([CH3:20])([CH3:19])[CH3:18])[CH:11]=[CH:12][C:3]=12

참가 물질

4

반응물 2

HCID 10942334Sodium MethoxideHCID 866767394-Chloro-1-[[2-(trimethylsilyl)ethoxy]methyl]-1H-pyrrolo[2,3-b]pyridine-5-carbaldehyde

생성물 1

HCID 866767404-Methoxy-1-[[2-(Trimethylsilyl)ethoxy]methyl]-1H-pyrrolo[2,3-b]pyridine-5-carbaldehyde수율 77%

시약·촉매·용매 1

HCID 887Methanol용매

반응 조건

온도
60 °C

실험 절차

Na (370 mg, 16.12 mmol) was dissolved in MeOH (5 mL) and 4-chloro-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrolo[2,3-b]pyridine-5-carbaldehyde (500 mg, 1.61 mmol) was added to the sodium methoxide solution. The reaction mixture was stirred for 8 hours for 60° C. The reaction mixture was quenched with water and the organic solvent was removed under reduced pressure. The resulting mixture was partitioned between ethyl acetate and water. The organic layer was separated and the aqueous layer was extracted with ethyl acetate. The combined organic extracts were washed with brine, dried over MgSO4, celite filtered and concentrated under reduced pressure. The crude product was purified by flash chromatography using (5% to 20% Ethyl acetate/Hexane) as a solvent to afford title compound (380 mg, 77% yield). 1H NMR (600 MHz, CDCl3) δ 10.51 (s, 1H), 8.74 (s, 1H), 7.36 (d, J=3.6 Hz, 1H), 6.90 (d, J=4.2 Hz, 1H), 5.72 (s, 2H), 4.48 (s, 3H), 3.60 (t, J=7.8 Hz, 2H), 0.97 (t, J=8.4 Hz, 2H), 0 (s, 9H). MS m/z: 307 [M+1].

후처리

  1. customThe reaction mixture was quenched with water
  2. customthe organic solvent was removed under reduced pressure
  3. customThe resulting mixture was partitioned between ethyl acetate and water
  4. customThe organic layer was separated
  5. extractionthe aqueous layer was extracted with ethyl acetate
  6. washThe combined organic extracts were washed with brine
  7. dry with materialdried over MgSO4, celite
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customThe crude product was purified by flash chromatography

출처 및 근거

ORD 기록
ord-7fd6c1f4f74a49e0889bf8be78f24679
출처 데이터셋
uspto-grants-2016_06
특허 번호
US09358231B2

반응 노트

불러오는 중…