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

HRID 472053Notes

Reaction equation

HRID 472053 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH:12]=[C:11]([C:14]2[C:22]3[C:17](=[CH:18][N:19]=[C:20]([C:23]4[C:28]([CH2:29][CH3:30])=[CH:27][CH:26]=[CH:25][C:24]=4[CH2:31][CH3:32])[CH:21]=3)[N:16]([CH:33]([CH2:37][CH2:38][CH3:39])[CH2:34][CH2:35][CH3:36])[CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>CCO.[Pd]>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]([C:14]2[C:22]3[C:17](=[CH:18][N:19]=[C:20]([C:23]4[C:24]([CH2:31][CH3:32])=[CH:25][CH:26]=[CH:27][C:28]=4[CH2:29][CH3:30])[CH:21]=3)[N:16]([CH:33]([CH2:37][CH2:38][CH3:39])[CH2:34][CH2:35][CH3:36])[CH:15]=2)[CH2:12][CH2:13]1)=[O:7])([CH3:2])([CH3:4])[CH3:3]

Participants

4

Reactant 1

HCID 671525954-[5-(2,6-diethyl-phenyl)-1-(1-propyl-butyl)-1H-pyrrolo[2,3-c]pyridin-3-yl]-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester

Product 1

HCID 582699614-[5-(2,6-diethyl-phenyl)-1-(1-propyl-butyl)-1H-pyrrolo[2,3-c]pyridin-3-yl]-piperidine-1-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

The 4-[5-(2,6-diethyl-phenyl)-1-(1-propyl-butyl)-1H-pyrrolo[2,3-c]pyridin-3-yl]-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester (50 mg, 0.10 mmol) is dissolved in EtOH (2 mL), 10% Pd/C (5 mg) is added, and the mixture is shook in a parr-reactor under 50 psi of H2 over 18 h. Filter, remove solvents and chromatograph the residue affords 4-[5-(2,6-diethyl-phenyl)-1-(1-propyl-butyl)-1H-pyrrolo[2,3-c]pyridin-3-yl]-piperidine-1-carboxylic acid tert-butyl ester as colorless oil: 1H NMR (CDCl3) 8.80 (s, 1H), 7.36 (s, 1H), 7.27 (t, J=7 Hz, 1H), 7.13 (d, J=12 Hz, 2H), 7.04 (s, 1H), 436 (m, 1H), 4.21 (m, 1H), 2.96 (m, 1H), 2.92 (m, 1H), 2.34 (m, 4H), 2.03 (m, 1H), 1.86 (m, 4H), 1.63 (m, 2H), 1.49 (s, 9H), 1.28 (m, 4H), 1.02 (t, J=8 Hz, 6H), 0.90 (t, J=8 Hz, 6H); LCMS m/z 532.39 (2.58 min).

Workup

  1. filtrationFilter
  2. customremove solvents and chromatograph the residue

Sources & evidence

ORD record
ord-c69ff44d1f4f40ef9f58b81f78113309
Source dataset
uspto-grants-2014_01
Patent number
US08633193B2

Reaction notes

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