HCID 22051064, compound → HCID 22051047, compound

HRID 1867036Notes

Reaction equation

HRID 1867036 reaction equation
[Br:1][C:2]1[C:3](=[O:25])[N:4]([CH2:18][C:19]2[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=2)[C:5]([CH3:17])=[CH:6][C:7]=1[C:8]#[C:9][C:10]1[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=1.[H][H]>C(OCC)(=O)C.CCO.O=[Pt]=O>[Br:1][C:2]1[C:3](=[O:25])[N:4]([CH2:18][C:19]2[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=2)[C:5]([CH3:17])=[CH:6][C:7]=1[CH2:8][CH2:9][C:10]1[CH:11]=[CH:12][C:13]([F:16])=[CH:14][CH:15]=1

Participants

6

Reactant 2

HCID 22051064HCID 22051064, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 22051047HCID 22051047, compoundYield 23.3%

Reagents, catalysts & solvents 3

HCID 345198Adams' catalystCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A suspension of 3-bromo-4-[(4-fluorophenyl)ethynyl]-6-methyl-1-(pyridin-3-ylmethyl)pyridin-2(1H)-one (0.430 g, 1.01 mmol) in Ethyl acetate (5 mL) and EtOH (5 mL), containing PtO2 (0.015 g) was stirred in an atmosphere of hydrogen (15 psi) in a Fischer-Porter bottle for 2 hours. The reaction mixture was filtered and the filtrate was concentrated to reduce volume. The material was purified by flash column chromatography (ethyl acetate). The appropriate fractions were combined and concentrated under reduced pressure to afford the desired product (0.0943 g, 22%) as a sticky semisolid after drying. 1H-NMR (CD3OD, 400 MHz) δ 8.46 (d, 2H, J=26.4 Hz), 7.60 (d, 1H, J=8.0 Hz), 7.41 (dd, 1H, J=4.8 Hz, 4.8 Hz), 7.21 (m, 2H), 6.97 (t, 2H, J=8.8 Hz), 6.24 (s, 1H), 5.43 (s, 2H), 2.93 (m, 4H), 2.31 (s, 3H); ES-HRMS m/z 401.0645/403.0603 (M+H calculated for C20H19N2OFBr requires 401.0659/403.0641).

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated
  3. customThe material was purified by flash column chromatography (ethyl acetate)
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-9f96e077214b40478451b83515926205
Source dataset
uspto-grants-2009_12
Patent number
US07629363B2

Reaction notes

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