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Sodium Carbonate → HCID 178515654, compound

HRID 384131
Notes
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Reaction equation

HRID 384131 reaction equation
Cl[C:2]1[N:7]=[C:6]([CH2:8][CH2:9][O:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]3[O:21][N:20]=[C:19]([OH:22])[CH:18]=3)=[CH:13][CH:12]=2)[CH:5]=[CH:4][CH:3]=1.[F:23][C:24]1[CH:29]=[CH:28][C:27](B(O)O)=[CH:26][CH:25]=1.C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.C(COC)OC>[F:23][C:24]1[CH:29]=[CH:28][C:27]([C:2]2[N:7]=[C:6]([CH2:8][CH2:9][O:10][C:11]3[CH:16]=[CH:15][C:14]([C:17]4[O:21][N:20]=[C:19]([OH:22])[CH:18]=4)=[CH:13][CH:12]=3)[CH:5]=[CH:4][CH:3]=2)=[CH:26][CH:25]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 2856454-Fluorophenylboronic acidHCID 178515655HCID 178515655, compound

Product 1

HCID 178515654HCID 178515654, compound

Reagents, catalysts & solvents 1

HCID 22508344DME dimethoxyethaneSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 5-(4-(2-(6-chloropyridin-2-yl)ethoxy)phenyl)isoxazol-3-ol (46.5 mg) in dimethoxyethane ethylene glycol dimethyl ether (3 ml), 18 mg of tetrakis triphenylphosphine palladium, 31 mg of 4-fluorophenylboronic acid and 0.2 ml of 2M aqueous sodium carbonate solution were added, and the reaction solution was stirred at 90° C. for 2 hours. The reaction solution was cooled, then diluted with a saturated saline solution, extracted with ethyl acetate, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue obtained was purified through reversed phase medium pressure liquid chromatography (ODS-AS-360-CC (by YMC), mobile phase: water-acetonitrile-0.1% trifluoroacetic acid). The solvent of the resultant fraction was diluted with ethyl acetate, washed with saturated sodium bicarbonate water, and then dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue obtained was purified by preparative thin layer chromatography (Kieselgel™ 60 F254, Art5744, made by Merck & Co., methanol/chloroform (1:9)) to afford the title compound as a brown solid.

Workup

  1. temperatureThe reaction solution was cooled
  2. additiondiluted with a saturated saline solution
  3. extractionextracted with ethyl acetate
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationThe solvent was distilled off under reduced pressure
  6. customthe residue obtained
  7. customwas purified through reversed phase medium pressure liquid chromatography (ODS-AS-360-CC (by YMC), mobile phase: water-acetonitrile-0.1% trifluoroacetic acid)
  8. additionThe solvent of the resultant fraction was diluted with ethyl acetate
  9. washwashed with saturated sodium bicarbonate water
  10. dry with materialdried over anhydrous magnesium sulfate
  11. distillationThe solvent was distilled off under reduced pressure
  12. customthe residue obtained
  13. customwas purified by preparative thin layer chromatography (Kieselgel™ 60 F254, Art5744, made by Merck & Co., methanol/chloroform (1:9))

Sources & evidence

ORD record
ord-d0326201dd334b81a4ca02e7f930a220
Source dataset
uspto-grants-2013_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08367708B2

Reaction notes

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