Ethanol → HCID 54767344, compound

HRID 1042631Notes

Reaction equation

HRID 1042631 reaction equation
[N:1]1[C:14]2[C:5](=[CH:6][CH:7]=[C:8]3[C:13]=2[CH:12]=[CH:11][NH:10][C:9]3=[O:15])[CH:4]=[CH:3][CH:2]=1.[CH3:16][CH2:17][OH:18]>[Ni]>[OH:18][C@H:17]1[CH2:12][CH2:13][CH2:8][CH2:7][C@@H:16]1[N:10]1[CH:11]=[CH:12][C:13]2[C:8](=[CH:7][C:6]([CH2:6][C:5]3[CH:14]=[N:1][CH:2]=[CH:3][CH:4]=3)=[C:5]3[C:14]=2[N:1]=[CH:2][CH:3]=[CH:4]3)[C:9]1=[O:15]

Participants

4

Reactant 2

HCID 702EthanolHCID 217862161,8-Phenanthrolin-7(8H)-one

Product 1

HCID 54767344HCID 54767344, compound

Reagents, catalysts & solvents 1

HCID 935NickelCatalyst2×

Procedure

A solution of 8-[(1S,2S)-2-hydroxycyclohexyl]-5-{[6-methylsulfanyl)pyridin-3-yl]methyl}-1,8-phenanthrolin-7(8H)-one (40 mg, 0.093 mmol) in EtOH (1.9 mL) was treated with 0.22 g of Raney nickel slurry and heated at reflux for 3 h. Additional Raney nickel slurry (0.25 g) was added and heating continued for 1 hour (h). The gray suspension was filtered through Celite. The resulting filtrate was concentrated and dried in vacuo. The crude material was purified via silica gel chromatography, eluting with 25-100% ethyl acetate in hexanes, followed by elution with 0-15% MeOH in CH2Cl2. The resultant off-white solid gave a proton NMR spectra consistent with theory and a mass ion (ES+) of 386.0 for [M+H]+: 1H NMR (400 MHz, CDCl3) δ 8.95 (dd, J=4.4, 1.6 Hz, 1H), 8.55 (d, J=1.6 Hz, 1H), 8.42 (dd, J=4.4, 1.2 Hz, 1H), 8.21 (s, 1H), 8.13 (dd, J=8.4, 1.6 Hz, 1H), 7.90 (d, J=7.2 Hz, 1H), 7.48 (d, J=7.6 Hz, 1H), 7.44 (dd, J=8.4, 4.0 Hz, 1H), 7.34-7.36 (m, 1H), 7.11 (dd, J=8.0, 4.8 Hz, 1H), 4.97 (br s, 1H), 4.39 (s, 2H), 3.90 (br s, 1H), 2.25-2.30 (m, 1H), 2.00-2.04 (m, 1H), 1.87 (d, J=8.0 Hz, 1H), 1.69-1.78 (m, 1H), 1.37-1.64 (m, 3H).

Workup

  1. temperatureheated
  2. temperatureat reflux for 3 h
  3. temperatureheating
  4. filtrationThe gray suspension was filtered through Celite
  5. concentrationThe resulting filtrate was concentrated
  6. customdried in vacuo
  7. customThe crude material was purified via silica gel chromatography
  8. washeluting with 25-100% ethyl acetate in hexanes
  9. washfollowed by elution with 0-15% MeOH in CH2Cl2
  10. customThe resultant off-white solid gave a proton NMR spectra consistent with theory

Sources & evidence

ORD record
ord-a08fd3b9df6d4cb9bca87600d65256ef
Source dataset
uspto-grants-2013_10
Patent number
US08557992B2

Reaction notes

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