Hydrochloric Acid → HCID 22344545, compound

HRID 583914Notes

Reaction equation

HRID 583914 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:20])[C:7]=1[C:8]1[O:9][CH2:10][CH:11]([C:13]2[CH:18]=[CH:17][C:16](I)=[CH:15][CH:14]=2)[N:12]=1.[CH2:21]([O:23][C:24]1[CH:29]=[CH:28][C:27](B(O)O)=[CH:26][CH:25]=1)[CH3:22].C(=O)([O-])[O-].[Na+].[Na+].C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.Cl>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>[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:20])[C:7]=1[C:8]1[O:9][CH2:10][CH:11]([C:13]2[CH:18]=[CH:17][C:16]([C:27]3[CH:28]=[CH:29][C:24]([O:23][CH2:21][CH3:22])=[CH:25][CH:26]=3)=[CH:15][CH:14]=2)[N:12]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 80271Tri-o-tolylphosphineHCID 27343514-Ethoxyphenylboronic acidHCID 22344532HCID 22344532, compound

Product 1

HCID 22344545HCID 22344545, compound

Reagents, catalysts & solvents 1

HCID 178418476HCID 178418476, compoundCatalyst

Procedure

A solution of 2-(3,5-dichloro-4-pyridinyl)-4-(4-iodophenyl)oxazoline (0.2 g, 0.48 mmol), p-ethoxybenzeneboronic acid (0.095 g, 0.57 mmol), sodium carbonate (0.076 g, 0.72 mmol), dichlorobis(triphenylphosphine)palladium(II) (0.025 g) and tri-o-tolylphosphine (0.020 g) was heated at reflux for 12 h under an atmosphere of nitrogen. After cooling, 1N HCl (15 mL) was added and the mixture was extracted with diethyl ether (3×30 mL). The combined ether layers were dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by chromatography (eluant, ether/hexane—1:1) to give the product as an off-white solid: mp 121-122° C.

Workup

  1. temperatureat reflux for 12 h under an atmosphere of nitrogen
  2. temperatureAfter cooling
  3. extractionthe mixture was extracted with diethyl ether (3×30 mL)
  4. dry with materialThe combined ether layers were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by chromatography (eluant, ether/hexane—1:1)

Sources & evidence

ORD record
ord-2eb39c2086a2403097162251b7136300
Source dataset
uspto-grants-2005_08
Patent number
US06924298B2

Reaction notes

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