Trifluoroacetic acid → 3-ethyl-1H-pyrrolo[2,3-c]pyridine

HRID 2382086Notes

Reaction equation

HRID 2382086 reaction equation
[NH:1]1[C:5]2=[CH:6][N:7]=[CH:8][CH:9]=[C:4]2[C:3]([C:10](=O)[CH3:11])=[CH:2]1.C(O)(C(F)(F)F)=O>>[CH2:10]([C:3]1[C:4]2[C:5](=[CH:6][N:7]=[CH:8][CH:9]=2)[NH:1][CH:2]=1)[CH3:11]

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 118297291-(1H-pyrrolo(2,3-c)pyridin-3-yl)ethanone

Product 1

HCID 685549383-ethyl-1H-pyrrolo[2,3-c]pyridineYield 97%

Procedure

To a solution of 1-(1H-pyrrolo[2,3-c]pyridin-3-yl)-ethanone (1.53 g, 9.55 mmol) in TFA (29 mL) triethylsilane (6.88 g, 59.21 mmol) is added and stirred at rt for 18 h. The mixture is concentrated and extracted with EtOAc. The organic layer is washed with 2 N aqueous KOH, dried (Na2SO4), filtered and evaporated. The residue is chromatographed through silica gel eluting with 10% MeOH in DCM to afford 3-ethyl-1H-pyrrolo[2,3-c]pyridine (1.35 g, 97%). MS: 147 (M+H); 1H NMR (300 MHz, CDCl3): δ 13.3 (broad, N—H) 9.46 (s, 1H), 8.04 (s, 1H), 7.71-7.88 (m, 2H), 2.88 (q, 2H), 1.39 (t, 3H).

Workup

  1. concentrationThe mixture is concentrated
  2. extractionextracted with EtOAc
  3. washThe organic layer is washed with 2 N aqueous KOH
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue is chromatographed through silica gel eluting with 10% MeOH in DCM

Sources & evidence

ORD record
ord-c13234c2d9e14b15ac48316aa728269b
Source dataset
uspto-grants-2012_09
Patent number
US08258130B2

Reaction notes

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