Toluene → HCID 11397659, compound

HRID 131609Notes

Reaction equation

HRID 131609 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:27])[C:7]=1[NH:8][C:9]([C:11]1[C:19]2[C:18]3[CH:20]=[C:21]([NH2:24])[CH:22]=[CH:23][C:17]=3[O:16][C:15]=2[C:14]([O:25][CH3:26])=[CH:13][CH:12]=1)=[O:10].[C:28]([O:32][CH2:33][CH3:34])(=[O:31])[CH:29]=O.C1(C)C=CC=CC=1>C(O)C.[Ni]>[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:27])[C:7]=1[NH:8][C:9]([C:11]1[C:19]2[C:18]3[CH:20]=[C:21]([NH:24][CH2:29][C:28]([O:32][CH2:33][CH3:34])=[O:31])[CH:22]=[CH:23][C:17]=3[O:16][C:15]=2[C:14]([O:25][CH3:26])=[CH:13][CH:12]=1)=[O:10]

Participants

6

Reactant 3

HCID 1140TolueneHCID 70211Ethyl oxoacetateHCID 9978431HCID 9978431, compound

Product 1

HCID 11397659HCID 11397659, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

N-(3,5-dichloropyrid-4-yl)-4-methoxy-8-amino dibenzo[b,d]furan-1-carboxamide (500 mg, 1.24 mmol) was suspended in ethanol and a 50% solution of ethyl glyoxalate in toluene (384 mg, 3.72 mmol) was added to the suspension. The reaction mixture was hydrogenated at 40 psi in presence of pre-activated raney nickel (50% w/w) for 24 h-48 h. The reaction was filtered and the filterate was concentrated in vacuo. The residue was purified by silica gel (100-200) column chromatography using 0.5% methanol in dichloromethane to obtain the compound as a pale yellow solid (180 mg). mp: >270° C.

Workup

  1. filtrationThe reaction was filtered
  2. concentrationthe filterate was concentrated in vacuo
  3. customThe residue was purified by silica gel (100-200) column chromatography

Sources & evidence

ORD record
ord-10422d892f3f47af9f571fb1d9af8f5a
Source dataset
uspto-grants-2008_06
Patent number
US07384962B2

Reaction notes

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