Potassium Carbonate → HCID 86682416, compound

HRID 2365267Notes

Reaction equation

HRID 2365267 reaction equation
Br[C:2]1[CH:11]=[C:10]2[C:12](=[O:29])[N:13]([C@H:15]3[CH2:20][CH2:19][CH2:18][CH2:17][C@@H:16]3[O:21][Si:22]([C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:24])[CH3:23])[CH2:14][C:9]2=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2.[CH:30]([B-](F)(F)F)=[CH2:31].[K+].C(=O)([O-])[O-].[K+].[K+].C(=O)(O)[O-].[Na+]>C1COCC1.O.CC(C)([P](C(C)(C)C)([Pd][P](C(C)(C)C)(C(C)(C)C)C(C)(C)C)C(C)(C)C)C>[Si:22]([O:21][C@H:16]1[CH2:17][CH2:18][CH2:19][CH2:20][C@@H:15]1[N:13]1[CH2:14][C:9]2[C:10](=[CH:11][C:2]([CH:30]=[CH2:31])=[C:3]3[C:8]=2[N:7]=[CH:6][CH:5]=[CH:4]3)[C:12]1=[O:29])([C:25]([CH3:27])([CH3:26])[CH3:28])([CH3:24])[CH3:23]

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 516892Sodium BicarbonateHCID 23679353Potassium vinyltrifluoroborateHCID 86682407HCID 86682407, compound

Product 1

HCID 86682416HCID 86682416, compound

Reagents, catalysts & solvents 3

HCID 178418851HCID 178418851, compoundCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 5-bromo-8-[(1S,2S)-2-{[tert-butyl(dimethyl)silyl]oxy}cyclohexyl]-8,9-dihydro-7H-pyrrolo[3,4-h]quinolin-7-one (see Example 18, 2.00 g, 4.21 mmol) in a mixture of 20 mL of THF and 2 mL of water under an atmosphere of nitrogen was added potassium vinyltrifluoroborate (0.789 g, 5.89 mmol), potassium carbonate (1.45 g, 10.5 mmol), and bis(tri-tert-butylphosphine)palladium(0) (0.215 g, 0.421 mmol). The mixture was heated at 50° C. for 2 hr, cooled to ambient temperature, poured into saturated aqueous sodium bicarbonate and extracted 2× with ethyl acetate. The combined organic extracts were dried with sodium sulfate, filtered, and concentrated in vacuo. The residue was purified via silica gel chromatography, eluting with 0-60% ethyl acetate in hexanes to provide 8-[(1S,2S)-2{[tert-butyl(dimethyl)silyl]oxy}cyclohexyl]-5-ethenyl-8,9-dihydro-7H-pyrrolo[3,4-h]quinolin-7-one that gave a proton NMR spectra consistent with theory and a mass ion (ES+) of 424.4.

Workup

  1. temperaturecooled to ambient temperature
  2. extractionextracted 2× with ethyl acetate
  3. dry with materialThe combined organic extracts were dried with sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified via silica gel chromatography
  7. washeluting with 0-60% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-a3d46a9c25a44a03987a291755626d4b
Source dataset
uspto-grants-2014_04
Patent number
US08697690B2

Reaction notes

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