2-[4-(5-methylisoxazol-4-yl)phenyl]-N-[(1R)-1-(5-vinylpyridin-2-yl)ethyl]acetamide → N-[(1R)-1-(5-ethylpyridin-2-yl)ethyl]-2-[4-(5-methylisoxazol-4-yl)phenyl]acetamide

HRID 254694Notes

Reaction equation

HRID 254694 reaction equation
[CH3:1][C:2]1[O:6][N:5]=[CH:4][C:3]=1[C:7]1[CH:12]=[CH:11][C:10]([CH2:13][C:14]([NH:16][C@@H:17]([C:19]2[CH:24]=[CH:23][C:22]([CH:25]=[CH2:26])=[CH:21][N:20]=2)[CH3:18])=[O:15])=[CH:9][CH:8]=1.[H][H]>CCOC(C)=O.[Pd]>[CH2:25]([C:22]1[CH:23]=[CH:24][C:19]([C@H:17]([NH:16][C:14](=[O:15])[CH2:13][C:10]2[CH:11]=[CH:12][C:7]([C:3]3[CH:4]=[N:5][O:6][C:2]=3[CH3:1])=[CH:8][CH:9]=2)[CH3:18])=[N:20][CH:21]=1)[CH3:26]

Participants

5

Reactant 2

HCID 247655772-[4-(5-methylisoxazol-4-yl)phenyl]-N-[(1R)-1-(5-vinylpyridin-2-yl)ethyl]acetamideHCID 178418361HCID 178418361, compound

Product 1

HCID 24765576N-[(1R)-1-(5-ethylpyridin-2-yl)ethyl]-2-[4-(5-methylisoxazol-4-yl)phenyl]acetamide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 0.11 g (0.32 mmol) 2-[4-(5-methylisoxazol-4-yl)phenyl]-N-[(1R)-1-(5-vinylpyridin-2-yl)ethyl]acetamide in 1.30 ml EtOAc was added 0.010 g of 10% palladium on carbon. The reaction flask was equipped with a hydrogen balloon. After 24 h at room temperature, the reaction mixture was filter through celite, washed three times with methanol, and concentrated in vacuo. Purification by automated flash chromatography (40 g silica gel cartridge 20-100% EtAOc/hex over 15 min) afforded N-[(1R)-1-(5-ethylpyridin-2-yl)ethyl]-2-[4-(5-methylisoxazol-4-yl)phenyl]acetamide 1H NMR (CDCl3, 400 MHz) 8.35 (s, 1H); 8.31 (d, 1H, J=1.56 hz); 7.47 (dd, 1H, J=2.19 Hz, 7.96 Hz); 7.36 (d, 4H, J=2.29 Hz); 7.13 (d, 1H, J=7.88 Hz); 6.97 (br d, 1H J=7.88 Hz); 5.10 (m, 1H); 3.62 (s, 2H); 2.63 (q, 2H, J=7.60 Hz, 15.11 Hz); 2.57 (s, 3H); 1.43 (d, 3H, J=6.69); 1.24 (t, 3H, J=7.60). HRMS (ES) exact mass calcd for C21H23N3O2: 350.1864, Found: 350.1856.

Workup

  1. filtrationthe reaction mixture was filter through celite
  2. washwashed three times with methanol
  3. concentrationconcentrated in vacuo
  4. customPurification by automated flash chromatography (40 g silica gel cartridge 20-100% EtAOc/hex over 15 min)

Sources & evidence

ORD record
ord-88f6144e6d954042b3302b561f06a29c
Source dataset
uspto-grants-2011_01
Patent number
US07875636B2

Reaction notes

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