Cesium carbonate → 4-[5-(2,6-Diethyl-phenyl)-1H-pyrrolo[2,3-c]pyridin-3-yl]-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester

HRID 472051Notes

Reaction equation

HRID 472051 reaction equation
[CH2:1]([C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH2:9][CH3:10])[C:4]=1[C:11]1[CH:12]=[C:13]2[CH:19]=[CH:18][NH:17][C:14]2=[CH:15][N:16]=1)[CH3:2].[C:20]([O:24][C:25]([N:27]1[CH2:32][CH2:31][C:30](=O)[CH2:29][CH2:28]1)=[O:26])([CH3:23])([CH3:22])[CH3:21].C([O-])([O-])=O.[Cs+].[Cs+]>CO>[C:20]([O:24][C:25]([N:27]1[CH2:28][CH:29]=[C:30]([C:19]2[C:13]3[C:14](=[CH:15][N:16]=[C:11]([C:4]4[C:5]([CH2:9][CH3:10])=[CH:6][CH:7]=[CH:8][C:3]=4[CH2:1][CH3:2])[CH:12]=3)[NH:17][CH:18]=2)[CH2:31][CH2:32]1)=[O:26])([CH3:23])([CH3:21])[CH3:22]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 116732465-(2,6-diethyl-phenyl)-1H-pyrrolo[2,3-c]pyridine

Product 1

HCID 671525864-[5-(2,6-Diethyl-phenyl)-1H-pyrrolo[2,3-c]pyridin-3-yl]-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 5-(2,6-diethyl-phenyl)-1H-pyrrolo[2,3-c]pyridine (200 mg, 0.90 mmol), 4-oxo-piperidine-1-carboxylic acid tert-butyl ester (358 mg, 1.8 mmol), Cs2CO3 (586 mg, 1.8 mmol), and MeOH (6 mL) is refluxed for 18 h. MeOH is removed under reduced pressure. The residue is treated with acetic acid (0.5 mL) and water (3 mL) and is extracted with EtOAc. The combined organic extracts are washed with brine, dried over Na2SO4, and concentrated under reduced pressure. Chromatography of the residue affords 4-[5-(2,6-Diethyl-phenyl)-1H-pyrrolo[2,3-c]pyridin-3-yl]-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester as colorless oil.

Workup

  1. temperatureis refluxed for 18 h
  2. customMeOH is removed under reduced pressure
  3. additionThe residue is treated with acetic acid (0.5 mL) and water (3 mL)
  4. extractionis extracted with EtOAc
  5. washThe combined organic extracts are washed with brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-bd77b5089048426188045a8bc4685287
Source dataset
uspto-grants-2014_01
Patent number
US08633193B2

Reaction notes

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