Potassium Carbonate → HCID 67194734, compound

HRID 2366974Notes

Reaction equation

HRID 2366974 reaction equation
[C:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10](Br)=[CH:11][CH:12]=2)[CH:7]([NH:15][C:16](=[O:21])[O:17][CH:18]([CH3:20])[CH3:19])[CH2:6][CH:5]1[CH3:22])(=[O:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].OB(O)[C:31]1[O:32][CH:33]=[CH:34][C:35]=1[C:36]([OH:38])=[O:37].[OH-].[Na+:41]>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.C1(C)C=CC=CC=1.C(O)C>[C:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([C:31]3[O:32][CH:33]=[CH:34][C:35]=3[C:36]([O-:38])=[O:37])=[CH:11][CH:12]=2)[C@@H:7]([NH:15][C:16]([O:17][CH:18]([CH3:20])[CH3:19])=[O:21])[CH2:6][C@H:5]1[CH3:22])(=[O:3])[CH3:2].[Na+:41]

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 467390092-Boronofuran-3-carboxylic acidHCID 67197028HCID 67197028, compound

Product 1

HCID 67194734HCID 67194734, compoundYield 15%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 1140TolueneSolvent

Procedure

A flask was charged with 1-methylethyl (1-acetyl-6-bromo-2-methyl-1,2,3,4-tetrahydro-4-quinolinyl)carbamate (for a preparation see Example 61) (100 mg, 0.271 mmol), potassium carbonate (74.9 mg, 0.542 mmol), 2-(dihydroxyboranyl)-3-furancarboxylic acid (50.7 mg, 0.325 mmol) and tetrakis(triphenylphosphine)palladium(0) (15.65 mg, 0.014 mmol) then filled with ethanol (1 mL) and toluene (1 mL) and the resulting mixture was refluxed under nitrogen for 21 h then cooled to room temperature and partitioned between a 2M HCl aqueous solution (40 mL) and EtOAc (40 mL). The layers were separated and the aqueous phase was extracted with EtOAc (2×40 mL). The combined organic phases were washed with brine (80 mL), dried over Na2SO4 and concentrated in vacuo. Purification of the residue using MDAP (modifier; trifluoroacetic acid) gave a residue which was treated with a 2M NaOH aqueous solution (2.25×10−2 mL, 4.50 mmol). The precipitate formed was filtered off and dried under house vacuum to give sodium 2-[(2R,4S)-1-acetyl-2-methyl-4-({[(1-methylethyl)oxy]carbonyl}amino)-1,2,3,4-tetrahydro-6-quinolinyl]-3-furancarboxylate (18 mg, 0.040 mmol, 15%) as a cream solid.

Workup

  1. temperaturethe resulting mixture was refluxed under nitrogen for 21 h
  2. custompartitioned between a 2M HCl aqueous solution (40 mL) and EtOAc (40 mL)
  3. customThe layers were separated
  4. extractionthe aqueous phase was extracted with EtOAc (2×40 mL)
  5. washThe combined organic phases were washed with brine (80 mL)
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated in vacuo
  8. customPurification of the residue
  9. customgave a residue which
  10. customThe precipitate formed
  11. filtrationwas filtered off
  12. customdried under house vacuum

Sources & evidence

ORD record
ord-fd4b8c42139b4ed9b99625278d6ba547
Source dataset
uspto-grants-2014_04
Patent number
US08697725B2

Reaction notes

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