HCID 66678632, compound → HCID 10251668, compound

HRID 902041Notes

Reaction equation

HRID 902041 reaction equation
[CH3:1][O:2][C:3](=[O:32])[CH:4]=[CH:5][C:6]1[CH:15]=[C:14]2[C:9]([C:10]([C:16]3[C:17]([C:25]4[CH:30]=[CH:29][CH:28]=[C:27]([CH3:31])[N:26]=4)=[N:18][N:19]4[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=34)=[CH:11][CH:12]=[N:13]2)=[CH:8][CH:7]=1.[H][H]>CO.ClCCl.[Pd]>[CH3:1][O:2][C:3](=[O:32])[CH2:4][CH2:5][C:6]1[CH:15]=[C:14]2[C:9]([C:10]([C:16]3[C:17]([C:25]4[CH:30]=[CH:29][CH:28]=[C:27]([CH3:31])[N:26]=4)=[N:18][N:19]4[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=34)=[CH:11][CH:12]=[N:13]2)=[CH:8][CH:7]=1

Participants

6

Reactant 2

HCID 66678632HCID 66678632, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 10251668HCID 10251668, compoundYield 59%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

Add Pd/C (10%, 0.46 g) to a solution of 3-{4-[2-(6-methyl-pyridin-2-yl)-pyrazolo[1,5-a]pyridin-3-yl]-quinolin-7-yl}-acrylic acid methyl ester (0.462 g, 1.1 mmol) in MeOH (10 mL) and dichloromethane (10 mL). Bubble nitrogen for 15 minutes. Connect the hydrogen balloon to the reaction flask and stir overnight. Filter through celite and wash the celite pad with dichloromethane (50 mL). Remove the solvent. Chromatograph the residue (elute with 2% MeOH in dichloromethane) to give the desired product as a pale yellow solid 0.27 g (59%).

Workup

  1. filtrationFilter through celite
  2. washwash the celite pad with dichloromethane (50 mL)
  3. customRemove the solvent
  4. washChromatograph the residue (elute with 2% MeOH in dichloromethane)

Sources & evidence

ORD record
ord-41efeaac4f454aa19ab29e2d4c20becb
Source dataset
uspto-grants-2008_04
Patent number
US07365066B2

Reaction notes

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