Hexane → 4-methoxy-1-((2-(trimethylsilyl)ethoxy)methyl)-5-vinyl-1H-pyrrolo[2,3-b]pyridine

HRID 709317노트

반응식

HRID 709317 반응식
[I-].[CH3:2][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Li]CCCC.CCCCCC.[CH3:33][O:34][C:35]1[C:40]([CH:41]=O)=[CH:39][N:38]=[C:37]2[N:43]([CH2:46][O:47][CH2:48][CH2:49][Si:50]([CH3:53])([CH3:52])[CH3:51])[CH:44]=[CH:45][C:36]=12>C1COCC1>[CH3:33][O:34][C:35]1[C:40]([CH:41]=[CH2:2])=[CH:39][N:38]=[C:37]2[N:43]([CH2:46][O:47][CH2:48][CH2:49][Si:50]([CH3:53])([CH3:52])[CH3:51])[CH:44]=[CH:45][C:36]=12

참가 물질

6

반응물 4

HCID 8058HexaneHCID 638159Methyltriphenylphosphonium iodideHCID 866767404-Methoxy-1-[[2-(Trimethylsilyl)ethoxy]methyl]-1H-pyrrolo[2,3-b]pyridine-5-carbaldehydeHCID 178418339Butyllithium

생성물 1

HCID 673458184-methoxy-1-((2-(trimethylsilyl)ethoxy)methyl)-5-vinyl-1H-pyrrolo[2,3-b]pyridine수율 76%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution methyltriphenylphosphonium iodide (782 mg, 1.93 mmol) in dried THF (5 mL) was added 2.5 M n-BuLi in Hexane (0.74 mL, 1.85 mmol) at −78° C. After 10 minutes, 4-methoxy-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrolo[2,3-b]pyridine-5-carbaldehyde (493 mg, 1.61 mmol) was added to the reaction mixture. The reaction mixture was warmed to room temperature spontaneously. After 2 hours, the reaction mixture was quenched with water and 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 15% Ethyl acetate/Hexane) as a solvent to afford title compound (371 mg, 76% yield). 1H NMR (600 MHz, CDCl3) δ 8.40 (s, 1H), 7.27 (d, J=3.6 Hz, 1H), 7.07 (dd, J=11.4, 18 Hz, 1H), 6.78 (d, J=3.6 Hz, 1H), 5.78 (d, J=18 Hz, 1H), 5.70 (s, 2H), 5.30 (d, J=11.4 Hz, 1H), 4.38 (s, 3H), 3.60 (t, J=8.4 Hz, 2H), 0.97 (t, J=8.4 Hz, 2H), 0 (s, 9H). MS m/z: 305 [M+1].

후처리

  1. waitAfter 2 hours
  2. customthe reaction mixture was quenched with water
  3. customwas 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-c7d12d8806104968a96a83c708bb41d6
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09180127B2

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