HCID 89784303, compound → HCID 89783690, compound

HRID 1055936Notes

Reaction equation

HRID 1055936 reaction equation
[C:1]1([C:7]([C:9]2[CH:18]=[CH:17][C:16]3[C:11](=[C:12]([C:19]4[NH:27][C:26]5[CH2:25][CH2:24][NH:23][C:22](=[O:28])[C:21]=5[CH:20]=4)[CH:13]=[CH:14][CH:15]=3)[N:10]=2)=[CH2:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>[Pd].CO>[C:1]1([CH:7]([C:9]2[CH:18]=[CH:17][C:16]3[C:11](=[C:12]([C:19]4[NH:27][C:26]5[CH2:25][CH2:24][NH:23][C:22](=[O:28])[C:21]=5[CH:20]=4)[CH:13]=[CH:14][CH:15]=3)[N:10]=2)[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 1

HCID 89784303HCID 89784303, compound

Product 1

HCID 89783690HCID 89783690, compoundYield 79%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Conditions

Temperature
25 °C

Procedure

A suspension of 2-(2-(1-phenylvinyl)quinolin-8-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (Example 113; 102.4 mg, 0.280 mmol) and palladium on carbon (10% w/w; 59.6 mg, 0.056 mmol) in MeOH (3.0 mL) was cycled under a H2 gas atmosphere (1 atm; 3 evacuation/H2 back-fill cycles) and then stirred at 25° C. for 1 d. The mixture was filtered through Celite, washing the filter cake with MeOH (10 mL). The combined filtrates were concentrated in vacuo to provide rac-2-(2-(1-phenylethyl)quinolin-8-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (81.0 mg, 0.220 mmol, 79% yield) as a yellow-orange solid: 1H NMR (400 MHz, CDCl3) δ ppm 12.91 (1H, br. s.), 8.07-8.13 (2H, m), 7.60 (1H, dd, J=8.0, 1.0 Hz), 7.48-7.54 (1H, m), 7.35 (1H, d, J=6.8 Hz), 7.32-7.34 (2H, m), 7.29 (3H, d, J=6.8 Hz), 7.21 (1H, d, J=2.0 Hz), 5.38 (1H, br. s.), 4.54 (1H, q, J=7.0 Hz), 3.64 (2H, td, J=6.8, 2.5 Hz), 2.87-2.93 (2H, m), 1.87 (3H, d, J=7.0 Hz). m/z (ESI, +ve) 368.3 (M+H)+. Separation of this material by supercritical-fluid chromatography (Chiralcel OJ (250×21 mm, 10 μm), 50% liquid CO2/50% MeOH (+40 mM NH3), 50 mL/min) separately afforded 2-(2-(1-phenylethyl)quinolin-8-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one, first-eluting enantiomer (115; 30.5 mg, 0.083 mmol) and 2-(2-(1-phenylethyl)quinolin-8-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one, second eluting enantiomer (116; 27.6 mg, 0.075 mmol).

Workup

  1. filtrationThe mixture was filtered through Celite
  2. washwashing the filter cake with MeOH (10 mL)
  3. concentrationThe combined filtrates were concentrated in vacuo

Sources & evidence

ORD record
ord-6e80232c907743309d6d22f99493fc8f
Source dataset
uspto-grants-2016_07
Patent number
US09394297B2

Reaction notes

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