6-Azaindole → tert-Butyl 4-{1H-pyrrolo[2,3-c]pyridin-3-yl}-1,2,3,6-tetrahydropyridine-1-carboxylate

HRID 588401

Reaction equation

HRID 588401 reaction equation
[NH:1]1[C:5]2=[CH:6][N:7]=[CH:8][CH:9]=[C:4]2[CH:3]=[CH:2]1.O=[C:11]1[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH2:12]1.[OH-].[K+]>CO>[NH:1]1[C:5]2=[CH:6][N:7]=[CH:8][CH:9]=[C:4]2[C:3]([C:11]2[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH:12]=2)=[CH:2]1

Participants

5

Reactant 3

HCID 92196-AzaindoleHCID 14797Potassium HydroxideHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylate

Product 1

HCID 59559369tert-Butyl 4-{1H-pyrrolo[2,3-c]pyridin-3-yl}-1,2,3,6-tetrahydropyridine-1-carboxylateYield 92%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A suspension of 1H-pyrrolo[2,3-c]pyridine (0.95 g, 8.05 mmol), tert-butyl 4-oxo-piperidine-1-carboxylate (1.70 g, 8.54 mmol) and KOH (0.95 g, 17.0 mmol) in MeOH (10 mL) was heated at reflux overnight. The mixture was added to ice-water (50 mL) and then MeOH (50 mL) was added. The resulting solution was concentrated to circa 50 mL and then extracted three times with DCM/MeOH (9:1, 50 mL). The organic layers were combined and concentrated and the residue was purified by flash chromatography (9:1 DCM/MeOH) to yield the title compound as a light yellow solid (2.21 g, 92%). MS (ESI+) m/z=300 (M+H)+.

Workup

  1. temperaturewas heated
  2. temperatureat reflux overnight
  3. concentrationThe resulting solution was concentrated to circa 50 mL
  4. extractionextracted three times with DCM/MeOH (9:1, 50 mL)
  5. concentrationconcentrated
  6. customthe residue was purified by flash chromatography (9:1 DCM/MeOH)

Sources & evidence

ORD record
ord-ef0c13e8c0354ee09168905c946e3d4d
Source dataset
uspto-grants-2016_01
Patent number
US09227967B2

Linked notes

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