HCID 86681849, compound → HCID 66665673, compound

HRID 406212Notes

Reaction equation

HRID 406212 reaction equation
[C:1]1([CH3:36])[CH:6]=[CH:5][C:4]([C:7]2[N:8]=[C:9]3[CH2:23][CH2:22][CH2:21][N:20]([CH2:24][CH2:25][CH2:26][CH2:27][CH2:28]/[CH:29]=[CH:30]/[C:31]([O:33][CH2:34][CH3:35])=[O:32])[C:10]3=[N:11][C:12]=2[C:13]2[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=2)=[CH:3][CH:2]=1>CO.[Pd]>[C:1]1([CH3:36])[CH:2]=[CH:3][C:4]([C:7]2[N:8]=[C:9]3[CH2:23][CH2:22][CH2:21][N:20]([CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][C:31]([O:33][CH2:34][CH3:35])=[O:32])[C:10]3=[N:11][C:12]=2[C:13]2[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=2)=[CH:5][CH:6]=1

Participants

4

Reactant 1

HCID 86681849HCID 86681849, compound

Product 1

HCID 66665673HCID 66665673, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of (E)-ethyl 8-(2,3-dip-tolyl-7,8-dihydropyrido[2,3-b]pyrazin-5(6H)-yl)oct-2-enoate (step 1)(60 mg, 0.124 mmol) and 10% Pd/C (66.0 mg, 0.062 mmol) in MeOH (10 ml) placed under an atmosphere of hydrogen at 0.35 bar pressure and stirred at room temperature overnight. The mixture was filtered through Celite® (filter material) and washed through with MeOH. The filtrated was concentrated in vacuo and purification of the crude product by chromatography on silica eluting with iso-hexane/EtOAc afforded the title compound as a pale yellow oil;

Workup

  1. filtrationThe mixture was filtered through Celite® (filter material)
  2. washwashed through with MeOH
  3. concentrationThe filtrated was concentrated in vacuo and purification of the crude product by chromatography on silica eluting with iso-hexane/EtOAc

Sources & evidence

ORD record
ord-0c344020f5de41948abd3a97dd5d4520
Source dataset
uspto-grants-2014_06
Patent number
US08754085B2

Reaction notes

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