Triethylsilane → 3-Ethyl-1H-pyrrolo[2,3-b]pyridine

HRID 2382081노트

반응식

HRID 2382081 반응식
[NH:1]1[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[C:3]([C:10](=O)[CH3:11])=[CH:2]1.C([SiH](CC)CC)C>C(O)(C(F)(F)F)=O>[CH2:10]([C:3]1[C:4]2[C:5](=[N:6][CH:7]=[CH:8][CH:9]=2)[NH:1][CH:2]=1)[CH3:11]

참가 물질

4

반응물 2

HCID 12052TriethylsilaneHCID 127782161-(1H-Pyrrolo[2,3-b]pyridin-3-yl)ethan-1-one

생성물 1

HCID 132853593-Ethyl-1H-pyrrolo[2,3-b]pyridine수율 74.3%

시약·촉매·용매 1

HCID 6422Trifluoroacetic acid용매

실험 절차

To a solution of 1-(1H-Pyrrolo[2,3-b]pyridin-3-yl)-ethanone (1.34 g, 8.38 mmol) in TFA (25 mL) is added triethylsilane (6.09 g, 52.4 mmol) and stirred at rt for 18 h. The mixture is concentrated, diluted with 2 N aqueous KOH solution and extracted three times with DCM. The combined organic layer is dried (Na2SO4), filtered and evaporated. The resulting residue is chromatographed through silica gel eluting with 10% MeOH in DCM to afford 3-ethyl-1H-pyrrolo[2,3-b]pyridine (0.91 g). MS: 147 (M+H); 1H NMR (300 MHz, CDCl3): δ 9.23 (broad s, 1H), 8.32 (d, 1H), 7.94 (s, 1H), 7.05-7.14 (m, 2H), 2.80 (q, 2H), 1.35 (t, 3H).

후처리

  1. concentrationThe mixture is concentrated
  2. additiondiluted with 2 N aqueous KOH solution
  3. extractionextracted three times with DCM
  4. dry with materialThe combined organic layer is dried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated
  7. customThe resulting residue is chromatographed through silica gel eluting with 10% MeOH in DCM

출처 및 근거

ORD 기록
ord-83abdf97e81c456681c3793909a10404
출처 데이터셋
uspto-grants-2012_09
특허 번호
US08258130B2

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