Cesium carbonate → 2-Methyl-4-(pyridin-2-yloxy)-benzoic acid ethyl ester

HRID 1480975Notes

Reaction equation

HRID 1480975 reaction equation
[CH2:1]([O:3][C:4](=[O:13])[C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][C:6]=1[CH3:12])[CH3:2].I[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=1.CC(C)(C(=O)CC(=O)C(C)(C)C)C.C(=O)([O-])[O-].[Cs+].[Cs+]>CN1C(=O)CCC1.CCOC(C)=O.Cl[Cu]>[CH2:1]([O:3][C:4](=[O:13])[C:5]1[CH:10]=[CH:9][C:8]([O:11][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=2)=[CH:7][C:6]=1[CH3:12])[CH3:2]

Participants

8

Reactant 4

HCID 10796Cesium carbonateHCID 707002,2,6,6-Tetramethyl-3,5-heptanedioneHCID 2211262-IodopyridineHCID 13356900Ethyl 4-hydroxy-2-methylbenzoate

Product 1

HCID 898129622-Methyl-4-(pyridin-2-yloxy)-benzoic acid ethyl ester

Reagents, catalysts & solvents 3

HCID 62652Cuprous chlorideCatalystHCID 8857Ethyl AcetateSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 4-hydroxy-2-methyl-benzoic acid ethyl ester (400 mg), 2-iodo-pyridine (0.29 mL), CuCl (110 mg), 2,2,6,6-tetramethyl-heptane-3,5-dione (TMHD, 0.087 mL), cesium carbonate (940 mg) in NMP (2 mL) was heated at 120° C. for 20 h. Then the reaction was cooled, diluted with EtOAc, solids were filtered off, filtrate was washed with water, diluted NaCl solution, dried over sodium sulfate, filtered off, concentrated, the residue was column purified to give the desired product (531 mg). LC MS ESI+: 258 (M+1)+.

Workup

  1. temperatureThen the reaction was cooled
  2. filtrationwere filtered off
  3. washfiltrate was washed with water, diluted NaCl solution
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered off
  6. concentrationconcentrated
  7. custompurified

Sources & evidence

ORD record
ord-c9b0bb9f2ca34bcfaab8c9fa8d3220bf
Source dataset
uspto-grants-2016_08
Patent number
US09409892B2

Reaction notes

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