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

HRID 2382081Notes

Reaction equation

HRID 2382081 reaction equation
[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]

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-83abdf97e81c456681c3793909a10404
Source dataset
uspto-grants-2012_09
Patent number
US08258130B2

Reaction notes

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