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

HRID 2382081ノート

反応式

HRID 2382081 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6422Trifluoroacetic acid溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-83abdf97e81c456681c3793909a10404
出典データセット
uspto-grants-2012_09
特許番号
US08258130B2

反応ノート

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