1H-Pyrrolo(2,3-b)pyridine → Tert-butyl 4-(1H-pyrrolo[2,3-B]pyridin-3-YL)-5,6-dihydropyridine-1(2H)-carboxylate

HRID 1675029Notes

Reaction equation

HRID 1675029 reaction equation
[OH-].[K+].[NH:3]1[C:7]2=[N:8][CH:9]=[CH:10][CH:11]=[C:6]2[CH:5]=[CH:4]1.O=[C:13]1[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][CH2:14]1>CO>[NH:3]1[C:7]2=[N:8][CH:9]=[CH:10][CH:11]=[C:6]2[C:5]([C:13]2[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][CH:14]=2)=[CH:4]1

Participants

5

Reactant 3

HCID 92221H-Pyrrolo(2,3-b)pyridineHCID 14797Potassium HydroxideHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylate

Product 1

HCID 45790246Tert-butyl 4-(1H-pyrrolo[2,3-B]pyridin-3-YL)-5,6-dihydropyridine-1(2H)-carboxylateYield 54.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
65 °C

Procedure

Potassium hydroxide (1.90 g, 33.86 mmol) was added to 1H-pyrrolo[2,3-b]pyridine (1.0 g, 8.46 mmol) and tert-butyl 4-oxopiperidine-1-carboxylate (3.37 g, 16.93 mmol) in methanol (25 mL) at ambient temperature, then the resulting solution was stirred at 65° C. for 18 hours. The mixture was cooled to ambient temperature, quenched in dilute aqueous ammonium chloride (80 mL) and extracted with ethyl acetate. The extract was washed sequentially with water and saturated brine, dried over MgSO4, concentrated by evaporation and purified by flash silica chromatography, using 5% MeOH in DCM eluent. Pure fractions were combined and concentrated by evaporation, then triturated with ether to give a colourless precipitate. The precipitate was collected by filtration, washed with ether and air dried to afford tert-butyl 4-(1H-pyrrolo[2,3-b]pyridin-3-yl)-5,6-dihydropyridine-1(2H)-carboxylate (1.37 g, 54%) as a colourless solid.

Workup

  1. temperatureThe mixture was cooled to ambient temperature
  2. customquenched in dilute aqueous ammonium chloride (80 mL)
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed sequentially with water and saturated brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated by evaporation
  7. custompurified by flash silica chromatography
  8. concentrationconcentrated by evaporation
  9. customtriturated with ether
  10. customto give a colourless precipitate
  11. filtrationThe precipitate was collected by filtration
  12. washwashed with ether and air
  13. customdried

Sources & evidence

ORD record
ord-e02d7fbdde1a47a2bc83f588ebf77257
Source dataset
uspto-grants-2011_08
Patent number
US08003649B2

Reaction notes

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