Quinoline → HCID 57672434, compound

HRID 2101758Notes

Reaction equation

HRID 2101758 reaction equation
[CH3:1][C:2]([C:5]1[C:10]([C:11]2[CH:16]=[C:15]([O:17][CH3:18])[CH:14]=[CH:13][C:12]=2[F:19])=[CH:9][C:8]([CH2:20][O:21][C:22]2[CH:27]=[CH:26][C:25]([C@@H:28]([C:34]#[C:35][CH3:36])[CH2:29][C:30]([O:32][CH3:33])=[O:31])=[CH:24][CH:23]=2)=[CH:7][CH:6]=1)([CH3:4])[CH3:3].CCOC(C)=O.N1C2C(=CC=CC=2)C=CC=1>[Pd].CC([O-])=O.CC([O-])=O.[Pb+2]>[CH3:4][C:2]([C:5]1[C:10]([C:11]2[CH:16]=[C:15]([O:17][CH3:18])[CH:14]=[CH:13][C:12]=2[F:19])=[CH:9][C:8]([CH2:20][O:21][C:22]2[CH:23]=[CH:24][C:25]([C@@H:28](/[CH:34]=[CH:35]\[CH3:36])[CH2:29][C:30]([O:32][CH3:33])=[O:31])=[CH:26][CH:27]=2)=[CH:7][CH:6]=1)([CH3:1])[CH3:3]

Participants

5

Reactant 3

HCID 7047QuinolineHCID 8857Ethyl AcetateHCID 57672455HCID 57672455, compound

Product 1

HCID 57672434HCID 57672434, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 131709914Lindlars catalystCatalyst

Procedure

To a stirred solution of 4.2 (0.055 g, 0.11 mmol) in EtOAc (4.00 mL, 41 mmol) at 23° C. was added quinoline (0.500 mL, 4.2 mmol) followed by Lindlar's Catalyst (0.012 g, 0.11 mmol). The reaction mixture was placed under an atmosphere of hydrogen and stirring was continued for 40 hours. The mixture was filtered through a pad of silica gel. The filtrate was washed with 1N HCl (3×10 mL), and the organic layer was dried over MgSO4 and concentrated in vacuo. The residue was then purified by flash chromatography (SiO2 gel 60, eluted with 0%-20% EtOAc in hexanes) to give compound 8.1 as a clear oil (0.0529 g, 96% yield). MS ESI (pos.) m/e: 513.3 (M+Na)+, 508.3 (M+H2O)+.

Workup

  1. filtrationThe mixture was filtered through a pad of silica gel
  2. washThe filtrate was washed with 1N HCl (3×10 mL)
  3. dry with materialthe organic layer was dried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was then purified by flash chromatography (SiO2 gel 60, eluted with 0%-20% EtOAc in hexanes)

Sources & evidence

ORD record
ord-425a00a8c21b4c6a97d6c4326eada425
Source dataset
uspto-grants-2009_08
Patent number
US07572934B2

Reaction notes

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