Ethyl Acetate → HCID 178438028, compound

HRID 921525Notes

Reaction equation

HRID 921525 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[N:8](C(OCC)C)[N:9]=[C:10]([CH2:11][CH3:12])[C:3]=12.[N:18]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:21]=[C:20](B(O)O)[CH:19]=1.C(=O)([O-])[O-].[Na+].[Na+].C(OCC)(=O)C>COCCOC.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O>[CH2:11]([C:10]1[C:3]2[C:4](=[N:5][CH:6]=[CH:7][C:2]=2[C:20]2[CH:19]=[N:18][C:27]3[C:22]([CH:21]=2)=[CH:23][CH:24]=[CH:25][CH:26]=3)[NH:8][N:9]=1)[CH3:12]

Participants

8

Reactant 4

HCID 8857Ethyl AcetateHCID 10340Sodium CarbonateHCID 2734663Quinoline-3-boronic acidHCID 67500911HCID 67500911, compound

Product 1

HCID 178438028HCID 178438028, compoundYield 29%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
85 °C

Procedure

Tetrakis(triphenylphosphine)palladium(0) (0.69 g) was added to a solution of compound (3d) (3.01 g), quinoline-3-boronic acid (2.67 g), and an aqueous sodium carbonate solution (2 M, 23 mL) in ethylene glycol dimethyl ether (30 mL) under a nitrogen atmosphere, followed by stirring at 85° C. for 25 hr. The reaction solution was distributed between ethyl acetate and water. The organic layer was washed with saturated saline and then dried over anhydrous sodium sulfate. After distillation of the solvent, 1,4-dioxane (23 mL) and 6 N hydrochloric acid (23 mL) were added to the residue, and the resulting mixture was stirred at room temperature for 90 min. The pH was adjusted to 7 with an aqueous sodium hydroxide solution, followed by extraction with ethyl acetate. The organic layer was washed with saturated saline. The organic layer after the washing was dried over anhydrous sodium sulfate, and then the solvent was distilled away. The residue was purified by neutral silica gel column chromatography (n-hexane/ethyl acetate) to obtain compound (3e) (0.942 g, the second stage yield: 29%) as a white solid.

Workup

  1. washThe organic layer was washed with saturated saline
  2. dry with materialdried over anhydrous sodium sulfate
  3. distillationAfter distillation of the solvent, 1,4-dioxane (23 mL) and 6 N hydrochloric acid (23 mL)
  4. additionwere added to the residue
  5. stirringthe resulting mixture was stirred at room temperature for 90 min
  6. extractionfollowed by extraction with ethyl acetate
  7. washThe organic layer was washed with saturated saline
  8. dry with materialThe organic layer after the washing was dried over anhydrous sodium sulfate
  9. distillationthe solvent was distilled away
  10. customThe residue was purified by neutral silica gel column chromatography (n-hexane/ethyl acetate)

Sources & evidence

ORD record
ord-123d9eae761549789b8f43506a76a69c
Source dataset
uspto-grants-2016_03
Patent number
US09273045B2

Reaction notes

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