Ethanol → HCID 59175974, compound

HRID 1094514Notes

Reaction equation

HRID 1094514 reaction equation
Cl[C:2]1[N:7]=[C:6]([O:8][C:9]2[CH:10]=[C:11]3[C:16](=[CH:17][CH:18]=2)[C:15]([C:19]([OH:21])=[O:20])=[CH:14][CH:13]=[CH:12]3)[CH:5]=[CH:4][N:3]=1.C[CH2:23][OH:24].CCN([CH2:30][CH3:31])CC.[C]=[O:33]>CCOC(C)=O.C(O)(=O)CC(CC(O)=O)(C(O)=O)O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH2:30]([O:33][C:23]([C:2]1[N:7]=[C:6]([O:8][C:9]2[CH:18]=[CH:17][C:16]3[C:11](=[CH:12][CH:13]=[CH:14][C:15]=3[C:19]([OH:21])=[O:20])[CH:10]=2)[CH:5]=[CH:4][N:3]=1)=[O:24])[CH3:31]

Participants

8

Reactant 4

HCID 702EthanolHCID 8471TriethylamineHCID 24822776HCID 24822776, compoundHCID 178418416HCID 178418416, compound

Product 1

HCID 59175974HCID 59175974, compound

Reagents, catalysts & solvents 3

HCID 178418476HCID 178418476, compoundCatalystHCID 311Citric AcidSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 5 g (16.6 mMol) 6-(2-chloro-pyrimidin-4-yloxy)-naphthalene-1-carboxylic acid, 80 ml EtOH, 7 ml (50 mMol) Et3N and 1180 mg (1.6 mMol) PdCl2(PPh3)2 is stirred under a atmosphere of 120 bar carbonmonoxide in an autoclave for 12 h at 115° C. The reaction mixture is diluted with 500 ml EtOAc and 500 ml 10% citric acid. The aq. layer is separated off and extracted with 2 Portions of EtOAc. The organic phases are washed with water and brine, dried (Na2SO4) and concentrated. Trituration of the residue in EtOAc and filtration gives the title compound. More product can be isolated from the filtrate by chromatography (Combi Flash; CH2Cl2/EtOAc 4:1→EtOAc): m.p.: 214-217° C.; MS: [M+1]+=339; TLC(EtOAc+0.5% HOAc): Rf=0.30.

Workup

  1. customThe aq. layer is separated off
  2. extractionextracted with 2 Portions of EtOAc
  3. washThe organic phases are washed with water and brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. filtrationTrituration of the residue in EtOAc and filtration

Sources & evidence

ORD record
ord-4e7fcf940c524ae9998931b1edbd6578
Source dataset
uspto-grants-2012_03
Patent number
US08133886B2

Reaction notes

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