Tetrahydrofuran → 1H-Pyrrolo[2,3-b]pyridine-5-carbaldehyde

HRID 269484Notes

Reaction equation

HRID 269484 reaction equation
Br[C:2]1[CH:3]=[C:4]2[CH:10]=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1.C([Li])CCC.C1C[O:19][CH2:18]C1>>[NH:8]1[C:5]2=[N:6][CH:7]=[C:2]([CH:18]=[O:19])[CH:3]=[C:4]2[CH:10]=[CH:9]1

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 103079325-bromo-1H-pyrrolo[2,3-b]pyridineHCID 178418339Butyllithium

Product 1

HCID 228320511H-Pyrrolo[2,3-b]pyridine-5-carbaldehydeYield 61%

Procedure

To 5-Bromo-1H-pyrrolo[2,3-b]pyridine (1.5 g, 7.61 mmol) in THF (200 mL) at −78 C, under nitrogen, was added n-butyl lithium (2.5M in hexanes, 15.2 mmol, 6.1 mL), and the reaction solution was stirred with an overhead motor. After 1 hr, the resulting orange gel was quenched with methylormate (4.56 g, 76 mmol) and the reaction solution was allowed to slowly warm to 23C. The solution was poured into water and extracted with ethyl acetate, dried (Na2SO4) to give 1H-Pyrrolo[2,3-b]pyridine-5-carbaldehyde (0.68 g, 61% yield) as a yellow solid.

Workup

  1. customthe resulting orange gel was quenched with methylormate (4.56 g, 76 mmol)
  2. temperatureto slowly warm to 23C
  3. additionThe solution was poured into water
  4. extractionextracted with ethyl acetate
  5. dry with materialdried (Na2SO4)

Sources & evidence

ORD record
ord-3b9e9163534f455486a7ea1532947e3e
Source dataset
uspto-grants-2008_11
Patent number
US07446199B2

Reaction notes

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