Ethyl Acetate → HCID 10150326, compound

HRID 1866878Notes

Reaction equation

HRID 1866878 reaction equation
[CH2:1]([N:8]1[CH:13]=[CH:12][C:11]([C:14]#[C:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[C:10]([Br:22])[C:9]1=[O:23])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCOC(C)=O.[H][H]>[Pt]=O.CCO>[CH2:1]([N:8]1[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[C:10]([Br:22])[C:9]1=[O:23])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 22050204HCID 22050204, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 10150326HCID 10150326, compound

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 702EthanolSolvent

Procedure

A mixture of 1-benzyl-3-bromo-4-(phenylethynyl)pyridin-2(1H)-one (0.3 g), and platinum oxide (0.05 g) in a solvent mixture of EtOAc (10.0 mL) and EtOH (10.0 mL) was stirred in an atmosphere of hydrogen at 15 psi in a Fischer porter bottle for 45 min. The catalyst was removed by filtration, and filtrate was concentrated. The resulting residue was purified by silica gel flash chromatography using 25% EtOAc in hexanes as the eluent. The appropriate fractions (visualized under an UV lamp) were combined and concentrated under reduced pressure. 1H-NMR (CD3OD) δ: 7.56 (d, 1H, J=6.8 Hz), 7.31-7.17 (m, 10H), 6.24 (d, 1H, J=6.8 Hz), 5.19 (s, 2H), 2.96 (m, 2H), and 2.91 (m, 2H); ES-MS m/z=368 (MH+); HR-MS m/z (MH+) calcd C20H19NOBr 368.0650, found 368.0630.

Workup

  1. customThe catalyst was removed by filtration, and filtrate
  2. concentrationwas concentrated
  3. customThe resulting residue was purified by silica gel flash chromatography
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-4b7717dd908e42838eb6ec95d478ffac
Source dataset
uspto-grants-2009_12
Patent number
US07629363B2

Reaction notes

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