Phenol → HCID 66872788, compound

HRID 1967525Notes

Reaction equation

HRID 1967525 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(=O)([O-])[O-].[Cs+].[Cs+].CC(C)(C(=O)CC(=O)C(C)(C)C)C.CN1CCCC1.Br[C:34]1[CH:35]=[C:36]([O:57][CH3:58])[C:37]([NH:40][C:41](=[O:56])[C:42]2[CH:47]=[CH:46][CH:45]=[C:44]([S:48]([N:51]3[CH2:55][CH2:54][CH2:53][CH2:52]3)(=[O:50])=[O:49])[CH:43]=2)=[N:38][CH:39]=1>C(OCC)(=O)C.[Cu]Cl>[CH3:58][O:57][C:36]1[C:37]([NH:40][C:41](=[O:56])[C:42]2[CH:47]=[CH:46][CH:45]=[C:44]([S:48]([N:51]3[CH2:52][CH2:53][CH2:54][CH2:55]3)(=[O:50])=[O:49])[CH:43]=2)=[N:38][CH:39]=[C:34]([O:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH:35]=1

Participants

8

Reactant 5

HCID 996PhenolHCID 84541-MethylpyrrolidineHCID 10796Cesium carbonateHCID 707002,2,6,6-Tetramethyl-3,5-heptanedioneHCID 66872379N-(5-bromo-3-methoxypyridin-2-yl)-3-(pyrrolidin-1-ylsulfonyl)benzamide

Product 1

HCID 66872788HCID 66872788, compoundYield 8%

Reagents, catalysts & solvents 2

HCID 62652Cuprous chlorideCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
180 °C

Procedure

Phenol (21.4 mg), cesium carbonate (74.0 mg), copper(I) chloride (11.2 mg) and 2,2,6,6-tetramethylheptane-3,5-dione (2.1 mg) were added to an N-methylpyrrolidine (1.0 mL) solution of the compound (50.0 mg) obtained in Example 109 (Step 1), and with irradiation with microwaves, this was stirred at 180° C. for 20 minutes. The reaction liquid was diluted with ethyl acetate, and washed with water. The organic layer was dried with sodium sulfate, then filtered, and concentrated under reduced pressure. The residue was purified through reversed-phase HPLC (0.1% TFA acetonitrile/H2O=from 10% to 90%, gradient), and further purified through preparative thin-layer chromatography (NH silica gel, methanol/chloroform=10%) to give the entitled compound (4.0 mg, 8%) as a colorless oily substance.

Workup

  1. customwith irradiation with microwaves
  2. customThe reaction liquid
  3. washwashed with water
  4. dry with materialThe organic layer was dried with sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified through reversed-phase HPLC (0.1% TFA acetonitrile/H2O=from 10% to 90%, gradient)
  8. customfurther purified through preparative thin-layer chromatography (NH silica gel, methanol/chloroform=10%)

Sources & evidence

ORD record
ord-d456760aca914dafae93395275a82a8a
Source dataset
uspto-grants-2013_04
Patent number
US08420823B2

Reaction notes

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